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A kind of method of nitrile hydrolysis synthetic amide

A technology of nitrile hydrolysis and amide, which is applied in the preparation of carboxylic acid amides, chemical instruments and methods, and the preparation of organic compounds, etc., to achieve the effects of low catalyst load, good energy saving effect, and low reaction temperature

Inactive Publication Date: 2017-01-04
NANJING UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the reaction still has many deficiencies, such as high catalyst loading (5-10mol%), high reaction temperature (>100°C), and several times the equivalent of oxime (2-5equiv.)

Method used

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  • A kind of method of nitrile hydrolysis synthetic amide
  • A kind of method of nitrile hydrolysis synthetic amide
  • A kind of method of nitrile hydrolysis synthetic amide

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] Example 1: Benzamide

[0024]

[0025] Benzonitrile (103mg, 1mmol), [Cp*Rh(H 2 O) 3 ][OTf] 2 (3.0 mg, 0.005 mmol, 0.5 mol%), acetaldehyde oxime (65 mg, 1.1 mmol) and water (1 ml) were sequentially added to a 25 ml Schlenk reaction flask. After the reaction mixture was reacted at 50°C for 6 hours, it was cooled to room temperature, water was removed by rotary evaporation, and the target product was obtained by column separation, yield: 87%

[0026] 1 H NMR (500MHz, CDCl 3 )δ7.82 (d, J=7.3Hz, 2H, ArH), 7.54-7.44 (m, 3H, ArH), 6.09 (br s, 2H, NH 2 ); 13 C NMR (125MHz, CDCl 3 )δ169.7, 133.4, 131.9, 128.5, 127.3.

Embodiment 2

[0027] Example 2: 4-Methylbenzamide

[0028]

[0029]

[0030] 4-Methylbenzonitrile (117mg, 1mmol), [Cp*Rh(H 2 O) 3 ][OTf] 2 (3.0 mg, 0.005 mmol, 0.5 mol%), acetaldehyde oxime (65 mg, 1.1 mmol) and water (1 ml) were sequentially added to a 25 ml Schlenk reaction flask. After the reaction mixture was reacted at 50°C for 6 hours, it was cooled to room temperature, water was removed by rotary evaporation, and the target product was obtained by column separation, yield: 87%

[0031] 1 H NMR (500MHz, DMSO-d 6 )δ8.13 (br s, 1H, NH), 8.02-7.97 (m, 4H, ArH), 7.55 (br s, 1H, NH), 3.87 (s, 3H, CH 3 ); 13 C NMR (125MHz, DMSO-d 6 )δ168.0, 141.1, 131.5, 128.7, 127.5, 20.9.

Embodiment 3

[0032] Example 3: 3,5-Dimethylbenzamide

[0033]

[0034] 3,5-Dimethylbenzonitrile (131mg, 1mmol), [Cp*Rh(H 2 O) 3 ][OTf] 2 (3.0 mg, 0.005 mmol, 0.5 mol%), acetaldehyde oxime (65 mg, 1.1 mmol) and water (1 ml) were sequentially added to a 25 ml Schlenk reaction flask. After the reaction mixture was reacted at 50°C for 6 hours, it was cooled to room temperature. , rotary evaporation to remove water, column separation to obtain the target product, yield: 84%

[0035] 1 H NMR (500MHz, DMSO-d 6 )δ7.86(br s, 1H, NH), 7.46(s, 2H, ArH), 7.22(br s, 1H, NH), 7.14(s, 1H, ArH), 2.29(s, 6H, 2xCH 3 ); 13 C NMR (125MHz, DMSO-d 6 )δ168.6, 137.5, 134.3, 132.7, 125.4, 21.0.

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Abstract

The invention discloses a method for synthesizing amide through nitrile hydrolysis. The method comprises the following steps: adding nitrile, acetaldoxime, water, a water-soluble rhodium complex to a reaction vessel, and cooling to room temperature after reaction of a reaction mixture for several hours at the temperature of 50-80 DEG C; and adding ethyl acetate for extraction so as to obtain an organic layer, and carrying out rotary evaporation to remove a solvent, thus obtaining a target product. Compared with a method for synthesizing amide through nitrile hydrolysis by using oxime as a water source in a transition metal catalysis process, the method has the advantages that a used catalyst is low in loading and does not contain a phosphine ligand seriously polluting environments, synthesis can be performed in air, and nitrogen protection is not needed; and therefore, the method meets the green chemistry requirements and has a wide development prospect.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis chemistry, and in particular relates to a synthesis method of amide derivatives. Background technique [0002] Amides are an important class of organic synthesis and pharmaceutical intermediates, which have a wide range of applications and scientific research value in industrial production and academic research. The traditional method for the synthesis of amides is through the reaction of carboxylic acid derivatives (eg, acid chlorides, anhydrides, and esters) with ammonia. Although widely used, the raw materials used in this method are highly toxic and corrosive to equipment. The reaction releases a large amount of energy and produces a large amount of waste acid. Sex is low. The other is under the condition of strong acid and high temperature, through the isomerization of oxime, the Beckmann rearrangement reaction occurs to directly generate the target product amide. Although this me...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C233/65C07C235/46C07C233/05C07C233/09C07C233/11C07C235/80C07C235/84C07C231/06C07D307/68C07D333/38C07D239/28
Inventor 李峰邹小媛王娜娜
Owner NANJING UNIV OF SCI & TECH
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