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Method for synthesizing 4-(aminomethyl)benzoic acid

A technology of aminomethylbenzoic acid and bromomethylbenzoic acid, applied in the field of pharmaceutical synthesis, can solve problems such as being unsuitable for industrial production, unable to purchase benzyl cyanohalide, poor in selectivity, etc., and achieves large industrial practical value, bromination reaction The effect of high selectivity and high utilization rate

Active Publication Date: 2022-01-14
SHENYANG RES INST OF CHEM IND
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The raw material p-cyanobenzyl halide used in this route cannot be purchased. If p-cyanotoluene is used to synthesize p-cyano benzyl halide by itself, there are few domestic suppliers of raw material p-cyanotoluene, and the price is high
[0008] Method five, the early synthesis method of p-bromomethylbenzoic acid, is to use p-toluic acid as raw material, chlorobenzene as solvent, bromine as bromine reagent, high temperature reflux reaction, bromine utilization rate is only half, low purity and high cost , not suitable for industrial production
"Guangdong Chemical Industry Journal" 2015, Volume 42, Issue 18, Page 19-20 "Research on the Synthesis of p-Bromomethylbenzoic Acid", reported that N-bromosuccinimide was produced using p-toluic acid as raw material It is a brominated reagent, and benzoyl peroxide is used as an initiator to synthesize p-bromomethylbenzoic acid, and the yield is only 78%. The selectivity is poor and the yield is low, so it is not suitable for industrialized production

Method used

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  • Method for synthesizing 4-(aminomethyl)benzoic acid
  • Method for synthesizing 4-(aminomethyl)benzoic acid
  • Method for synthesizing 4-(aminomethyl)benzoic acid

Examples

Experimental program
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Effect test

Embodiment 1

[0030] Synthesis of 4-aminomethylbenzoic acid route:

[0031]

[0032] 1) Add 40.85 g of toluine to the reaction bottle, 2.96 g of azo diisobutyronitrile, 45.46g of brombide (commercial procurement), industrial dichloromethane 327ml, reflow reaction, temperature 39 ° C, reaction 9h. Covered to 30 ° C, 59 ml of purified water was added, stirred for 1 h, filtered, and the filter cake was to bromine methylbenzoic acid, with a mass of 98.9%, purity 99.89%.

[0033] It can be seen from the above steps to employ the utilization of the bromide of the present invention is greater than 95%; and the utilization rate is less than 50%, which in the prior art uses the present invention to further reduce costs.

[0034] 2) Add a carbonate 67.96 g, 21% ammonia water from 193.55 g, purified water 185 ml, and stirred at room temperature, adding 43.01 g of bromomethylbenzoic acid, heating, at 50 ° C for 1 h in step 1. Filtration, the filtrate was concentrated to viscous, filtered, and cake. The f...

Embodiment 2

[0043] 1) Add 40.85 g of tolueneic acid to the reaction bottle, 0.99 g of azo diisobutyronitrile, 43.75 g of dibromo sea (this brominated agent is used in accordance with the secondary brombide synthesis method in Example 1, with the second Zai Sea was represented by raw materials, which was more than 98.0% of the purity of more than 98.0%), 163 ml of industrial dichloromethane, reflow reaction, temperature 39 ° C, reaction 12h. Covered to 30 ° C, 59 ml of purified water was added, stirred for 1 h, filtrate, and the filter cake was to bromide methylbenzoic acid, the mass was 98.3%, and the purity was 99.78%.

[0044] 2) Add carbonate 67.96 g, 21% ammonia water from 193.55 g, purified water 185 ml, and dissolved in step 1, and 10 ° C was added to 50 ° C for 1 h. Filtration, the filtrate was concentrated to viscous, filtered, and cake. The filter cake was added 193.55 g of ammonia water, stirred at room temperature, concentrated to the material pH = 7.5, filtered, the filter cake wa...

Embodiment 3

[0049] 1) Add 40.85 g of toluine to the reaction bottle, 2.50 g of azo diisobutyronitrile, 45.46 g of dibromo sea (this brominated agent is used in accordance with the two brombide synthesis methods in Example 1, with the second Zai Sea was represented by raw materials, which was greater than 98.0% of the purity of more than 98.0%), 327 ml of industrial grade 1,2-dichloroethane, reflow reaction, temperature 83 ° C, reaction for 6 h. Covered to 30 ° C, 59 ml of purified water was added, stirred for 1 h, filtered, and the filter cake was ptchlorobenzoic acid, the mass was 97.7%, and the purity was 99.71%.

[0050] 2) Add carbonate 67.96 g, 21% ammonia water from 193.55 g, purified water 185 ml, and dissolved in step 1, and 10 ° C was added to 50 ° C for 1 h. Filtration, the filtrate was concentrated to viscous, filtered, and cake. The filter cake was added 193.55 g of ammonia water, stirred at room temperature, concentrated to the material pH = 7.5, filtered, the filter cake was hig...

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Abstract

The invention belongs to the technical field of medicine synthesis, and particularly relates to a method for synthesizing 4-(aminomethyl)benzoic acid by using dibromohydantoin as a brominating agent. The method comprises the following steps: carrying out bromination reaction on p-toluic acid and dibromohydantoin in a solvent by using an initiator, carrying out suction filtration after the reaction, collecting a filter cake to obtain p-bromomethyl benzoic acid, and carrying out ammonification reaction on the p-bromomethyl benzoic acid to obtain the 4-(aminomethyl)benzoic acid. The 4-(aminomethyl)benzoic acid obtained by using the method is high in purity and low in cost, production safety is improved, the complexity and depreciation rate of equipment are reduced, and the method has a relatively large industrial practical value; and brominating reagents, namely hydantoin and bromine elements are well recycled, so production cost is reduced.

Description

Technical field [0001] The present invention belongs to the technical sequestration of drug synthesis, and more particularly to a method using dibromo sea as a bromine agent in a synthesis of 4-aminomethylbenzoic acid. Background technique [0002] Molechallic acid is a luggage, has excellent hemostasis and prevention of bleeding, suitable for abnormal hemorrhage, obstetric bleeding, obstetrics and gynecology and postpartum hemorrhage during surgery, adrenal, and postpartum hemorrhage, Blood, hematuria, prostate hypertetrients, upper gastrointestinal bleeding, etc. Aminoic acid also has to prevent and improve skin pigmentation, widely used in the field of medical and daily cultures. Molechallic acid is also a key intermediate that synthesizes another application a broader hemostatic drug amine acid, and the market demand is huge. [0003] The preparation method of amtroduve carnate mainly includes the following: [0004] Method 1. Patent CN201910225125.7 discloses a methylene emb...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C227/08C07C229/38C07C51/363C07C63/70C07D239/22
CPCC07C227/08C07C51/363C07D239/22C07C63/70C07C229/38Y02P20/55
Inventor 柴宝山王志强韩涛王云华朱君周龙邢久歌焦佳媛
Owner SHENYANG RES INST OF CHEM IND
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