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Method for preparing amide compound

A technology of amide compounds and compounds, which is applied in the field of organic compound preparation, can solve problems such as difficult control of the progress of the reaction, and achieve the effects of simple and controllable preparation process, improving efficiency, and inhibiting excessive hydrolysis

Inactive Publication Date: 2014-09-03
SUZHOU UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Under alkaline conditions, the hydrogen peroxide oxidation method can hydrolyze nitriles into amides in a short period of time at room temperature; but this method is usually not easy to control the progress of the reaction, and the cyano group is completely hydrolyzed into carboxylic acid

Method used

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  • Method for preparing amide compound
  • Method for preparing amide compound
  • Method for preparing amide compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] Dissolve 2-cyanopyridine (10 mmol, 1.04 g) and NaOH (0.1 mmol, 4 mg) in a mixed solvent of toluene / water (V:V=3:1), and stop the reaction after reflux for 6 hours. After standing at room temperature, the solvent was spin-dried, purified and separated by silica gel column chromatography to obtain 0.95 g of white solid 2-amidopyridine (yield: 78%); Ms (M / Z): 122.0 (M + ).

Embodiment 2

[0032] 2-cyanopyridine (10 mmol, 1.04 g), K 2 CO 3 (0.5 mmol, 69 mg) was dissolved in a mixed solvent of toluene / water / ethanol (V:V:V=6:2:1), and after 12 hours of reflux reaction, the reaction was stopped, and after standing at room temperature, the solvent was spin-dried Afterwards, use silica gel column chromatography to carry out purification and separation to obtain white solid 2-amidopyridine 1.04 g (yield: 85%); Ms (M / Z): 122.0 (M + ).

Embodiment 3

[0034] Dissolve 2-bromo-5-cyanopyridine (10 mmol, 1.83g), sodium tert-butoxide (0.1 mmol, 9.6 mg) in a mixed solvent of xylene / ethanol (V:V=3:1), and reflux After reacting for 4 hours, the reaction was stopped, and after standing at room temperature, the solvent was spin-dried, purified and separated by silica gel column chromatography to obtain 1.84 g of white solid 2-bromo-5-amidopyridine (yield: 92%); Ms (M / Z):201.0 (M + ).

[0035] The structural formula of above-mentioned 2-bromo-5-amide pyridine is:

[0036] .

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Abstract

The invention belongs to the field of organic compound preparation, and particularly relates to a method for preparing an amide compound. Specifically, cyano compounds are subjected to selective hydrolysis with a mixed solvent of a protic solvent and a non protonic solvent as a reaction medium under the conditions of heating and alkaline catalysis in the air atmosphere, so as to efficiently produce corresponding amide compounds; at the same time, carbon-carbon coupling reaction can be further utilized to react a compound containing cyano group and halogen group with a boronic acid compound, so as to prepare coupled amide compound through a one-step preparation method. The method avoids the usage of traditional toxic and harmful oxidants such as hydrogen peroxide, and is simple, efficient and green synthesis method for preparing the amide compound.

Description

technical field [0001] The invention belongs to the field of organic compound preparation, and in particular relates to a method for preparing amide compounds. Background technique [0002] Amide compounds are an important class of chemical raw materials, which are widely used in the fields of biology, medicine, and pharmacy. There are two ways to prepare amide compounds in the prior art: one is to prepare amides through the condensation reaction of carboxyl and amino groups, but this reaction usually requires activation of raw materials, and the reaction conditions are usually relatively harsh. [0003] In addition, amide compounds are prepared by hydrolysis of cyano group, which is mainly divided into hydrolysis of cyano group under acidic or alkaline conditions. Under alkaline conditions, the hydrogen peroxide oxidation method can hydrolyze nitriles to amides in a short period of time at room temperature; but this method is usually not easy to control the progress of the...

Claims

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Application Information

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IPC IPC(8): C07D213/81
CPCC07C231/06C07D213/81C07C233/11C07C233/65
Inventor 周宇扬王筱梅叶常青朱赛江徐鹏杰梁作芹
Owner SUZHOU UNIV OF SCI & TECH
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