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Application of urotropine as catalyst in aminomethylbenzoic acid synthesis

A technology for synthesizing aminotoluic acid and catalysts, applied in the preparation of organic compounds, cyanide reaction preparation, organic chemistry, etc., can solve the problems of high industrial production costs and low product yields, and achieve increased product yields and reduced production costs , the effect of reducing environmental pollution

Inactive Publication Date: 2012-12-12
SHANGHAI MODERN HASEN SHANGQIU PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0013] Although the catalysts used in these amination methods are cheap, easy to get, and have less environmental pollution, the product yields are all low, and the cost of industrial production is relatively high.

Method used

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  • Application of urotropine as catalyst in aminomethylbenzoic acid synthesis
  • Application of urotropine as catalyst in aminomethylbenzoic acid synthesis

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] At 10°C, 33.6g (0.24mol) of urotropine and 54.0g (3.0mol) of water were put into the reactor, stirred until completely dissolved, then 34.2g (0.2mol) of p-chloromethylbenzoic acid was added, stirred Evenly, pass ammonia gas until the reaction solution is completely dissolved, then heat to 40 ° C for 4 hours, and finally evaporate the ammonia under reduced pressure to pH 7-8, cool and crystallize, filter, and dry to obtain 21.1 g of aminotoluic acid (mol Yield 62.4%).

Embodiment 2

[0026] At 22°C, 44.9g (0.32mol) of urotropine and 61.2g (3.4mol) of water were put into the reactor, stirred until completely dissolved, then 34.2g (0.2mol) of p-chloromethylbenzoic acid was added, stirred Evenly, pass ammonia gas until the reaction solution is completely dissolved, then heat to 50°C and react for 4 hours, and finally evaporate the ammonia under reduced pressure to pH 7-8, cool and crystallize, filter, and dry to obtain 22.3 g of aminotoluic acid (mol Yield 65.9%).

Embodiment 3

[0028] At 30°C, 56.1g (0.40mol) of urotropine and 64.8g (3.6mol) of water were put into the reactor and stirred until it was completely dissolved, then 34.2g (0.2mol) of p-chloromethylbenzoic acid was added and stirred Evenly, pass ammonia gas until the reaction solution is completely dissolved, then heat to 60°C and react for 3 hours, and finally evaporate the ammonia under reduced pressure to pH 7-8, cool and crystallize, filter, and dry to obtain 21.8 g of aminotoluic acid (mol Yield 64.4%).

[0029] The results of the first six applications are shown in the table below:

[0030]

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PUM

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Abstract

The invention relates to application of urotropine as a catalyst in aminomethylbenzoic acid synthesis. The method comprises the following steps: at the temperature of 10-30 DEG C, dissolving urotropine in water, stirring until the urotropine is completely dissolved, adding p-chloromethylbenzoic acid or p-bromomethylbenzoic acid, stirring uniformly, slowly introducing ammonia gas within 1 hour until the reaction liquid is completely clear, heating to 40-60 DEG C to react for 3-4 hours, evaporating under reduced pressure to remove ammonia until the pH value is 7-8, cooling to crystallize, filtering, and drying to obtain the aminomethylbenzoic acid, wherein the filtrate can be continuously used repeatedly more than six times. By using the urotropine as the catalyst for aminating aminomethylbenzoic acid, compared with the prior art, the invention can greatly enhance the product yield, wherein the first-use yield of the catalyst is 60%, and the product yield of the repeatedly used mother solution can reach 70-80%, thereby greatly lowering the industrial production cost and reducing the environmental pollution.

Description

technical field [0001] The invention relates to the application of a new catalyst in the amination synthesis process of aminotoluic acid, which belongs to the field of chemical drug synthesis. Background technique [0002] The full name of aminotoluic acid is p-aminomethylbenzoic acid, also known as hemostatic aromatic acid and p-carboxybenzamine. The chemical name is p-aminomethylbenzoic acid monohydrate, and the English name is Axinoxethyl benzoic acid Xonohydrate. The chemical structural formula is: [0003] [0004] Molecular formula: C 8 h 9 NO 2 ·H 2 O, with a molecular weight of 169.18, is a procoagulant drug, suitable for various bleeding caused by fibrinolysis. Aminomethylbenzoic acid is also a raw material for the synthesis of tranexamic acid with a wider hemostatic range and better effect, see? Chinese Practical Medicine? 2011, Vol. [0005] At present, there are the following two synthesis routes for the amination of aminotoluic acid, see? Pharmaceutical ...

Claims

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Application Information

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IPC IPC(8): C07C229/38C07C227/08
Inventor 江正祥宋振峰刁文瑞
Owner SHANGHAI MODERN HASEN SHANGQIU PHARMA
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