WO1990009988A2 - Preparations d'amides - Google Patents
Preparations d'amides Download PDFInfo
- Publication number
- WO1990009988A2 WO1990009988A2 PCT/GB1990/000315 GB9000315W WO9009988A2 WO 1990009988 A2 WO1990009988 A2 WO 1990009988A2 GB 9000315 W GB9000315 W GB 9000315W WO 9009988 A2 WO9009988 A2 WO 9009988A2
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- process according
- aromatic
- reaction
- nitrile
- perborate
- Prior art date
Links
- 238000002360 preparation method Methods 0.000 title claims description 7
- 150000001408 amides Chemical class 0.000 title description 7
- 238000006243 chemical reaction Methods 0.000 claims abstract description 42
- 150000002825 nitriles Chemical class 0.000 claims abstract description 16
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims abstract description 15
- -1 aromatic nitrile Chemical class 0.000 claims abstract description 15
- 150000008430 aromatic amides Chemical class 0.000 claims abstract description 11
- 125000001424 substituent group Chemical group 0.000 claims abstract description 11
- 239000012429 reaction media Substances 0.000 claims abstract description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims abstract description 8
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims abstract description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims abstract description 6
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims abstract description 6
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims abstract description 6
- 229910052783 alkali metal Inorganic materials 0.000 claims abstract description 5
- 150000001340 alkali metals Chemical class 0.000 claims abstract description 5
- 230000001476 alcoholic effect Effects 0.000 claims abstract description 4
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 4
- IBDSNZLUHYKHQP-UHFFFAOYSA-N sodium;3-oxidodioxaborirane;tetrahydrate Chemical compound O.O.O.O.[Na+].[O-]B1OO1 IBDSNZLUHYKHQP-UHFFFAOYSA-N 0.000 claims abstract description 4
- XSVSPKKXQGNHMD-UHFFFAOYSA-N 5-bromo-3-methyl-1,2-thiazole Chemical compound CC=1C=C(Br)SN=1 XSVSPKKXQGNHMD-UHFFFAOYSA-N 0.000 claims abstract description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims abstract description 3
- 229930192474 thiophene Natural products 0.000 claims abstract description 3
- 125000001475 halogen functional group Chemical group 0.000 claims abstract 2
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract 2
- 238000000034 method Methods 0.000 claims description 29
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 9
- 239000011541 reaction mixture Substances 0.000 claims description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 125000004001 thioalkyl group Chemical group 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 125000003118 aryl group Chemical group 0.000 abstract description 5
- 125000002837 carbocyclic group Chemical group 0.000 abstract description 2
- 239000000758 substrate Substances 0.000 description 12
- 239000000047 product Substances 0.000 description 10
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- 239000002904 solvent Substances 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 230000008020 evaporation Effects 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 125000002560 nitrile group Chemical group 0.000 description 3
- 239000007800 oxidant agent Substances 0.000 description 3
- 238000007254 oxidation reaction Methods 0.000 description 3
- 230000001590 oxidative effect Effects 0.000 description 3
- 238000003860 storage Methods 0.000 description 3
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 125000001153 fluoro group Chemical group F* 0.000 description 2
- 125000005842 heteroatom Chemical group 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 230000003993 interaction Effects 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 150000002978 peroxides Chemical class 0.000 description 2
- DPZNOMCNRMUKPS-UHFFFAOYSA-N resorcinol dimethyl ether Natural products COC1=CC=CC(OC)=C1 DPZNOMCNRMUKPS-UHFFFAOYSA-N 0.000 description 2
- 239000012418 sodium perborate tetrahydrate Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 238000004809 thin layer chromatography Methods 0.000 description 2
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 1
- UEMGWPRHOOEKTA-UHFFFAOYSA-N 1,3-difluorobenzene Chemical compound FC1=CC=CC(F)=C1 UEMGWPRHOOEKTA-UHFFFAOYSA-N 0.000 description 1
- GJNGXPDXRVXSEH-UHFFFAOYSA-N 4-chlorobenzonitrile Chemical compound ClC1=CC=C(C#N)C=C1 GJNGXPDXRVXSEH-UHFFFAOYSA-N 0.000 description 1
- RPVGEEHGKIFQFO-UHFFFAOYSA-N 4-methylsulfanylbenzonitrile Chemical compound CSC1=CC=C(C#N)C=C1 RPVGEEHGKIFQFO-UHFFFAOYSA-N 0.000 description 1
- 125000000066 S-methyl group Chemical group [H]C([H])([H])S* 0.000 description 1
- 150000008431 aliphatic amides Chemical class 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 150000003934 aromatic aldehydes Chemical class 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 230000003292 diminished effect Effects 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 238000006703 hydration reaction Methods 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000012544 monitoring process Methods 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229960001922 sodium perborate Drugs 0.000 description 1
- YKLJGMBLPUQQOI-UHFFFAOYSA-M sodium;oxidooxy(oxo)borane Chemical compound [Na+].[O-]OB=O YKLJGMBLPUQQOI-UHFFFAOYSA-M 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 238000010183 spectrum analysis Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 125000004354 sulfur functional group Chemical group 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/81—Amides; Imides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/06—Preparation of carboxylic acid amides from nitriles by transformation of cyano groups into carboxamide groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/48—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
- C07D215/54—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 3
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D307/68—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D333/38—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
Definitions
- the present invention relates to the preparation of amides and more specifically to a process for theLr preparation from the corresponding nitrile. It is often desired to employ oxidising systems in carrying out reactions. When these are contemplated on a commercial scale, it is generally recognised that in an ideal world, it would be advantageous for such oxidising systems to be widely available, storage stable, easy to handle and relatively cheap, but also beneficial if they could also perform the desired reaction under mild conditions. Unfortunately, the world is often far from ideal, because the demands for good storage stability and safe handling of oxidising systems can be incompatible with the counter-demands of good reactivity at mild conditions.
- a process for preparing an aromatic amide from the corresponding aromatic nitrile in which the nitrile is contacted with an alkali metal perborate in an aqueous alcoholic reaction medium at a mild reaction temperature until at least some of the corresponding aromatic amide has been formed.
- the range of aromatic nitriles which are suitable starting materials for the present invention process is extremely wide. Results that were regarded as at least satisfactory were obtained from a very large number of different nitrile substituted compounds.
- the aromatic nucleus can comprise a carbocyclic nucleus or a nucleus substituted by a heteroatom.
- Suitable nuclei include benzene, furan, thiophene, pyridine or a fused ring system such as quinoline.
- Present trials have not demonstrated a positive result from a polycyclic carbocyclic nucleus, and such nuclei are deemed to be excluded herein from the term aromatic for the purpose of the present invention process unless or until they are shown to yield the desired product.
- the reaction has been demonstrated most often when the nitrile substituent is a direct substituent of the aromatic nucleus but an acceptable result has also been obtained when the nitrile was separated from the nucleus by an interposed methylene group. It will be understood, however, that the present invention process does not extend to the use of aliphatic nitriles as starting materials.
- the aromatic nucleus can be further substituted by a wide range of substituents, including both electron withdrawing and electron donating substituents, in any position around the nucleus, although it will be recognised that their presence will affect to a greater or lesser extent the efficiency of the reaction, depending also upon their position around the nucleus relative to the nitrile substituent. Whilst the invention process has been best characterised in the presence of a single additional substituent, a number of results demonstrate that a plurality of substituents can be present, provided that they are so positioned around the nucleus as to avoid shielding the nitrile from reaction, ie avoiding substitution simultaneously at the 2,6 positions by bulky groups, such as groups that are significantly larger than fluoro.
- Suitable substituents can be selected from alkyl groups, and especially methyl, halo groups, specifically chloro or fluoro groups, alkoxy, preferably methoxy groups, thioalkyl, such as thiomethyl, nitro or nitrile groups. It is also possible to employ substrates containing amino or hydroxyl groups although the efficiency of the present invention reaction in their presence is somewhat diminished, to the extent demonstrated by the examples provided herein.
- the present invention provides a convenient process for the preparation of a lagre number of substituted aromatic amides.
- the reaction employs an oxidising system, which is reduced by interaction with the substrate, it is possibly referred to more accurately as an hydrolysis reaction rather than as an oxidation reaction.
- the alkali perborate is particularly conveniently a sodium perborate on account of the bulk availability and excellent storage and handling properties of the two industrially available products sodium perborate monohydrate and sodium perborate tetrahydrate, which have respectively the empirical formulae aI.O3.H2O and a-.O3.4H2O, though these do not properly represent the structure of the compounds.
- a particularly safe way comprises introducing it progressively, such as in small portions or continuously during an introductory period, either at or below the desired reaction temperature.
- the invention reaction conditions permit the hydration reaction of the nitrile to be effected using only a modest excess of perborate.
- a mole ratio for perboraternitrile selected in the range of from at least 1.5:1 to 6:1 and particularly from 2.5:1 to 4:1.
- the efficiency of the reaction depending upon which substituents are present, but by appropriate selection of conditions, it is possible to obtain very high conversion to the amide at a mole ratio chosen within the aforementioned ranges.
- the reaction medium for the present reaction comprises an aqueous alcohol solution.
- the alcohol is particularly suitably a low molecular weight aliphatic alcohol, and especially one that is free from olefinic unsaturation.
- An advantageously convenient example comprises methanol.
- the ratio of alcohol : water in the reaction mixture is often chosen within the range of ratios of from 2:1 to 1:2 v/v.
- the alcohol component of the reaction medium can be introduced progressively, into a preformed aqueous mixture of the perborate, water and substrate, ie in portions or continuously throughout an extended period of reagent introduction.
- the reaction is carried out at a mild temperature, by which is meant that there is no need to maintain a high temperature during the reaction or even approach closely reflux temperature for the medium. In many instances, it is convenient to employ a temperature that is above ambient, and preferably above 40°C, up to about 70°C. Very effective oxidations have been achieved in the region of or around 45 to 55°C throughout the reaction period.
- the total reaction period will usually be determined in practice by taking into account the reaction temperature and the substrate and will often include a period during which perborate is introduced and a subsequent period in which the reaction is allowed to progress.
- the alcohol introduction period is often chosen within the range of 10 to 60 minutes.
- the subsequent period is often chosen in the range of from 45 minutes to 10 hours and for many of the substrates in the range of from 45 minutes to 200 minutes.
- Some reaction can occur whilst the alcohol is being introduced so that the total reaction period is often selected in the range of from 1 hour to 10 hours, and for many substrates from 1 hour to 4 hours.
- reaction can be monitored, for example by thin layer chromatography. Recovery of the product can be commenced when the monitoring indicates that either a desired proportion of the substrate has been consumed or converted to the product, or the consumption or production rate has slowed to a rate at or near zero, thereby indicating that little further product could be obtained.
- reaction periods can be gauged in small scale trials and refined in bulk-scale operation.
- the invention process is particularly suitable for a batch style reaction procedure, but it will be recognised that by a suitable choice of reactor design such as a once through tubular reactor, it is a practical proposition to carry out the reaction continuously, especially for those substrates that employ a relatively short reaction period.
- the product can be recovered from the reaction mixture by removal if desired of at least part of the alcohol from the reaction medium, such as by evaporation, preferably under reduced pressure, and subsequent addition of a stripping immiscible solvent to the residue, thereby transferring the product mainly into the solvent.
- Suitable solvents include halogenated hydrocarbons such as chloroform.
- the total amount of solvent employed is often chosen within the range of from 1 to 10 parts v/v per part of reaction mixture.
- the conventional techniques of solvent stripping, viz continuous co- or counter-current contact or multiple batch contact are applicable.
- the solvent can subsequently be removed, preferably by evaporation under reduced pressure to yield a solid product.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pyridine Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
On décrit une préparation d'amides aromatiques obtenues par la réaction d'un nitrile aromatique avec un perborate de métal alcalin en excès, de préférence un monohydrate ou un tétrahydrate de perborate de sodium, dans un milieu de réaction alcoolique, de préférence du méthanol, dans des conditions de réaction modérées comprises entre 40°C et 70°C. Le rapport moléculaire pour le perborate: nitrile est de préférence compris entre environ 2,5:1 et 4:1. Le nitrile aromatique peut être remplacé par une grande variété de substituants additionnels, tels que des groupes alkyle, halo, alkoxy thioalkyle ou nitro, et le noyau aromatique peut être carbocyclique ou hétérocyclique, y compris benzène, furane, thiophène, pyridine et quinoléine.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB898904799A GB8904799D0 (en) | 1989-03-02 | 1989-03-02 | Amide preparation |
| GB8904799.7 | 1989-03-02 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| WO1990009988A2 true WO1990009988A2 (fr) | 1990-09-07 |
| WO1990009988A3 WO1990009988A3 (fr) | 1990-10-18 |
Family
ID=10652608
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/GB1990/000315 WO1990009988A2 (fr) | 1989-03-02 | 1990-02-28 | Preparations d'amides |
Country Status (2)
| Country | Link |
|---|---|
| GB (1) | GB8904799D0 (fr) |
| WO (1) | WO1990009988A2 (fr) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105017053A (zh) * | 2015-07-16 | 2015-11-04 | 合肥祥晨化工有限公司 | 一种水杨酰胺的合成方法 |
| CN112495391A (zh) * | 2020-12-21 | 2021-03-16 | 中国科学院山西煤炭化学研究所 | 一种适用于乙腈水合反应制备乙酰胺的负载型复合金属催化剂及其制备方法和应用 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE828247C (de) * | 1948-10-02 | 1953-07-02 | Degussa | Verfahren zur Herstellung von Nicotinsaeureamid |
| NL131718C (fr) * | 1965-11-29 | |||
| US4222960A (en) * | 1978-06-08 | 1980-09-16 | Chemie Linz Aktiengesellschaft | Process for the manufacture of α-hydroxycarboxylic acid amides |
-
1989
- 1989-03-02 GB GB898904799A patent/GB8904799D0/en active Pending
-
1990
- 1990-02-28 WO PCT/GB1990/000315 patent/WO1990009988A2/fr unknown
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105017053A (zh) * | 2015-07-16 | 2015-11-04 | 合肥祥晨化工有限公司 | 一种水杨酰胺的合成方法 |
| CN112495391A (zh) * | 2020-12-21 | 2021-03-16 | 中国科学院山西煤炭化学研究所 | 一种适用于乙腈水合反应制备乙酰胺的负载型复合金属催化剂及其制备方法和应用 |
Also Published As
| Publication number | Publication date |
|---|---|
| WO1990009988A3 (fr) | 1990-10-18 |
| GB8904799D0 (en) | 1989-04-12 |
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