Preparation method of 2-amino-3-methyl-5-chlorobenzoic acid

A technology of methylbenzoic acid and chlorobenzoic acid, which is applied in the preparation of nitro compounds, organic compounds, and cyanide reaction preparations, and can solve problems such as large environmental pollution, low yield, and long reaction time

Active Publication Date: 2021-05-11
锦州三丰科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The raw material 7-methylindole-2,3-dione used in the method is expensive, and the chlorine gas is polluted to the environment, the reaction time is too long, and the yield is low

Method used

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  • Preparation method of 2-amino-3-methyl-5-chlorobenzoic acid
  • Preparation method of 2-amino-3-methyl-5-chlorobenzoic acid
  • Preparation method of 2-amino-3-methyl-5-chlorobenzoic acid

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preparation example Construction

[0029] The invention provides a kind of preparation method of 2-amino-3-methyl-5-chlorobenzoic acid, comprising the following steps:

[0030] Mixing m-toluic acid and nitric acid for nitration reaction to obtain 2-nitro-3-methylbenzoic acid, the mass concentration of the nitric acid is 60% to 75%;

[0031] Mixing the 2-nitro-3-methylbenzoic acid, a hydrogenation reduction reaction solvent and a hydrogenation catalyst, and performing a hydrogenation reduction reaction in a hydrogen atmosphere to obtain 2-amino-3-methylbenzoic acid;

[0032] The 2-amino-3-methylbenzoic acid, chlorination reagent, benzoyl peroxide and chlorination reaction solvent are mixed, and the chlorination reaction is carried out to obtain 2-amino-3-methyl-5-chlorobenzoic acid .

[0033] In the present invention, unless otherwise specified, the raw materials used are commercially available products well known to those skilled in the art.

[0034] The present invention takes m-toluic acid as raw material, ...

Embodiment 1

[0057] Add 400ml of nitric acid with a mass concentration of 65% into a 1L four-neck glass flask, cool down to -10°C, add 100g (0.734mol) of m-toluic acid in batches, and keep stirring at 0°C for 1 hour after the addition is completed. Phase chromatography detects that the area-normalized content of m-toluic acid is less than 0.3% to end the reaction, filter the obtained nitration reaction system, rinse and dry the solid with 100ml of cold water to obtain 106.2g of 2-nitro-3-methylbenzoic acid , the purity of 2-nitro-3-methylbenzoic acid determined by liquid phase is 98.7%, the yield is 79.8%, and the melting point is 217-219°C.

[0058] Add 106.2g (0.586mol) of 2-nitro-3-methylbenzoic acid to a 1L four-necked flask, add 318.6ml of ethanol, stir to dissolve, add 5.3g of 10% Pd / C, connect the four-necked flask to the hydrogen bag Finally, pass hydrogen through vacuuming, and cycle for 3 times to ensure that the air is completely removed, then pass hydrogen, the pressure of hydr...

Embodiment 2

[0063]Add 800ml of nitric acid with a mass concentration of 65% into a 2L four-neck glass flask, cool down to -10°C, add 200g (1.469mol) of m-toluic acid in batches, and keep stirring at -10°C for 1 hour after the addition, and pass through the liquid phase Chromatographically detects that the area-normalized content of m-toluic acid is less than 0.3% to end the reaction, filter the obtained nitration reaction system, and obtain 210.4 g of 2-nitro-3-methylbenzoic acid after the solid is rinsed with 200 ml of cold water and dried. The purity of 2-nitro-3-methylbenzoic acid determined by liquid phase was 98.8%, the yield was 79.0%, and the melting point was 217-219°C.

[0064] Add 210.4g (1.161mol) 2-nitro-3-methylbenzoic acid to a 2L four-necked flask, add 631ml of ethanol, stir to dissolve, add 10.5g10%Pd / C, connect the four-necked flask to the hydrogen bag, After evacuating, hydrogen gas is circulated for 3 times to ensure that the air is completely removed, and then hydrogen...

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Abstract

The invention belongs to the technical field of organic synthesis, and particularly relates to a preparation method of 2-amino-3-methyl-5-chlorobenzoic acid. The preparation method provided by the invention comprises the steps of mixing m-toluic acid and nitric acid, and carrying out nitration reaction to obtain 2-nitro-3-methyl benzoic acid, wherein the mass concentration of the nitric acid is 60-75%; mixing the 2-nitro-3-methyl benzoic acid, a hydrogenation reduction reaction solvent and a hydrogenation catalyst, and carrying out hydrogenation reduction reaction in a hydrogen atmosphere to obtain 2-amino-3-methyl benzoic acid; and mixing the 2-amino-3-methyl benzoic acid, a chlorination reagent, benzoyl peroxide and a chlorination reaction solvent, and carrying out a chlorination reaction to obtain the 2-amino-3-methyl-5-chlorobenzoic acid. The preparation method provided by the invention has the advantages of cheap and easily available reaction raw materials, high product yield and high purity, and is easy for industrial production.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and in particular relates to a preparation method of 2-amino-3-methyl-5-chlorobenzoic acid. Background technique [0002] Chlorantraniliprole pesticide is a kind of broad-spectrum insecticide, which is mainly used to control Lepidoptera pests of various crops, and has good control effect on other pests. Its mechanism of action is to activate ryanodine receptors and release Calcium stored in smooth muscle and striated muscle cells causes muscle regulation weakness, paralysis, until the death of pests, and the mode of action is stomach toxicity and contact toxicity. Chlorantraniliprole is also known as 3-bromo-N-[4-chloro-2-methyl-6-[(methylcarbamoyl)benzene]-1-(3-chloropyridin-2-yl)-1H- Pyrazole-5-carboxamide, English common name: chlorantraniliprole, CAS registration number: 500008-45-7, molecular formula: C 18 h 14 BrCl 2 N 5 o 2 , relative molecular mass: 483.1, and its chemical...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C227/16C07C229/56C07C201/08C07C205/57C07C227/04
CPCC07C201/08C07C227/04C07C227/16C07C205/57C07C229/56
Inventor 王栋伟赵宏洋王诚刘涛
Owner 锦州三丰科技有限公司
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