A kind of synthetic method of n-methyl-4-(methylamino)-3-nitrobenzamide

A technology of nitrobenzamide and nitrobenzoyl chloride, which is applied in the field of synthesis of N-methyl-4--3-nitrobenzamide, can solve the problem of high requirements for process equipment, expensive raw materials, and high production consumption. Time and other issues, to achieve the effects of easy large-scale promotion, simple synthesis process, and low production cost

Inactive Publication Date: 2016-06-08
SHANGHAI INST OF TECH
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Problems solved by technology

[0011] The purpose of the present invention is to solve the above-mentioned synthetic method of N-methyl-4-(methylamino)-3-nitrobenzamide with expensive raw materials, high process equipment requirements, long production time and low yield and other technical problems to provide a kind of N-methyl-4-(methylamino)-3-nitrobenzene with low raw material cost, low equipment requirements, simple synthesis process, easy operation, and a final yield of more than 95%. Synthetic method of formamide

Method used

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  • A kind of synthetic method of n-methyl-4-(methylamino)-3-nitrobenzamide

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Embodiment 1

[0038] A kind of synthetic method of N-methyl-4-(methylamino)-3-nitrobenzamide, described N-methyl-4-(methylamino)-3-nitrobenzamide The structural formula is as follows:

[0039]

[0040] where R 1 for CH 3 -, R 2 for CH 3 -, R 3 for NO 2 -.

[0041] The synthetic method of above-mentioned a kind of N-methyl-4-(methylamino)-3-nitrobenzamide specifically comprises the steps:

[0042](1) Add 4-chloro-3-nitrobenzoic acid (10g, 0.05mol) into a 100mL round bottom flask, add 30mL of 25% methylamine aqueous solution by mass percentage, and heat up in an oil bath under magnetic stirring conditions Return to the reflux state, react for 3-5 hours, cool and drop acetic acid to adjust the pH value to 3, and precipitate yellow 4-methylamino-3-nitrobenzoic acid crude product, rinse with a small amount of water, filter, and dry to obtain 4-methylaminobenzoic acid Amino-3-nitrobenzoic acid, yield 99.4%;

[0043] The amount of the 4-chloro-3-nitrobenzoic acid used in the above-ment...

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Abstract

The invention discloses a synthetic method of N-methyl-4-(methyl amino)-3-nitrobenzamide. The method comprises the following steps: firstly, 4-chloro-3-nitrobenzoic acid and methylamine react to generate 4-methyl amino-3-nitrobenzoic acid; then 4-methyl amino-3-nitrobenzoic acid and thionyl chloride have an acylating chlorination reaction to generate 4-(methyl amino)-3-nitrobenzoyl chloride; and finally, 4-(methyl amino)-3-nitrobenzoyl chloride and methylamine react to obtain the N-methyl-4-(methyl amino)-3-nitrobenzamide. The synthetic method of the N-methyl-4-(methyl amino)-3-nitrobenzamide has the advantages that raw material source is wide, the price and the production cost are low, the synthetic process is simple, the operation is simple and convenient, short time is consumed, the product yield is very high, and the total yield of the final product can reach 97.5%.

Description

technical field [0001] The invention relates to a synthesis method of N-methyl-4-(methylamino)-3-nitrobenzamide, belonging to the field of chemical synthesis. Background technique [0002] N-methyl-4-(methylamino)-3-nitrobenzamide is widely used as an intermediate of various drugs. It can be used as an intermediate of triazole derivatives with pharmacodynamic functions for treating diabetes, hypertension, insulin resistance, dementia, and schizophrenia, and can also be used as an intermediate for treating hereditary immunodeficiency, autoimmune diseases, and hematopoietic functions Disordered benzimidazole analogues. It can also be used as an intermediate in the synthesis of benzimidazole derivatives that can treat alopecia and promote hair growth. [0003] In 2010, the world patent WO2010001946 (A1) mentioned a synthesis method of the compound N-ethyl-4-(methylamino)-3-nitrobenzamide. In this synthesis method, an organic base was used as a catalyst , the reaction yield i...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C237/30C07C231/02
Inventor 任玉杰李良章王庆伟
Owner SHANGHAI INST OF TECH
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