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Method for preparing 2-hydroxy-4,5-dimethoxybenzoic acid

A technology of trimethoxybenzoic acid and dimethylacetamide, applied in the field of preparing intermediate 2-hydroxyl-4, which can solve the problem of strong volatility that is not conducive to labor protection, metal Lewis acid environmental problems, and the price of boron trifluoride ether More expensive and other problems, to achieve the effect of less impurities, short reaction time, suitable for industrial production

Inactive Publication Date: 2016-08-03
SHANGHAI INST OF PHARMA IND CO LTD +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The boron trifluoride diethyl ether used in this method is expensive, easy to decompose, and highly volatile, which is not conducive to labor protection. Metal Lewis acid has environmental problems and is not suitable for industrial production.

Method used

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  • Method for preparing 2-hydroxy-4,5-dimethoxybenzoic acid
  • Method for preparing 2-hydroxy-4,5-dimethoxybenzoic acid
  • Method for preparing 2-hydroxy-4,5-dimethoxybenzoic acid

Examples

Experimental program
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Effect test

Embodiment 1

[0020] N 2 Under air flow, 2.0 g of 2,4,5-trimethoxybenzoic acid and 5.45 g of piperazine were suspended in 10 ml of N,N-dimethylacetamide, heated and stirred at 150° C. for 2 hours to stop the reaction. 70°C water pump rotary steaming to constant weight, and then oil pump rotary steaming to constant weight. Adjust the pH, stir overnight at room temperature, filter with suction, and dry under reduced pressure to obtain 1.81 g of the product with a yield of 95.3%. m + 199, M+Na + 221.

Embodiment 2

[0022] N 2 Under air flow, 2.0 g of 2,4,5-trimethoxybenzoic acid and 5.45 g of piperazine were suspended in 10 ml of N,N-dimethylacetamide, heated and stirred at 140° C. for 1 hour to stop the reaction. 70°C water pump rotary steaming to constant weight, and then oil pump rotary steaming to constant weight. Adjust the pH, stir overnight at room temperature, filter with suction, and dry under reduced pressure to obtain 1.4 g of the product with a yield of 75%.

Embodiment 3

[0024] N 2 Under air flow, 2.0 g of 2,4,5-trimethoxybenzoic acid and 5.5 g of morpholine were suspended in N,N-dimethylacetamide, heated and stirred at 150° C. for 3 hours to stop the reaction. 70°C water pump rotary steaming to constant weight, and then oil pump rotary steaming to constant weight. Adjust the pH, stir overnight at room temperature, filter with suction, and dry under reduced pressure to obtain 1.5 g of the product with a yield of 80%.

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Abstract

The invention discloses a method for preparing a compound of formula (2). The method is characterized in that linear or annular amine reacts with a compound of formula (1) in a polar aprotic solvent to obtain the compound of formula (2). The method has the advantages of high yield, low cost, simple operation, and suitableness for the industrial production.

Description

technical field [0001] The present invention relates to a novel process for the preparation of the intermediate 2-hydroxy-4,5-dimethoxybenzoic acid. Background technique [0002] 2-Hydroxy-4,5-dimethoxybenzoic acid is the preparation of gastric motility drug N-[2-(diisopropylamino)ethyl]-2-[(2-hydroxy-4,5-dimethoxy Benzoyl)amino]-1,3-thiazole-4-carboxamide hydrochloride (Acotiamidehydrochloride, Z-338) is an important intermediate, and its synthesis has important economic value. [0003] Chinese patent application CN200580028537 describes the preparation of 2-hydroxy-4,5-dimethoxybenzoic acid: [0004] [0005] Use a Lewis acid such as boron trifluoride diethyl ether AlCl 3 As a selective demethylation reagent, it can be obtained by reacting with 2,4,5-trimethylbenzoic acid in the presence of an alkali metal bromide or alkali metal iodide in the presence of an ester, ketone, or amide solvent. The boron trifluoride diethyl ether used in the method is expensive, easy to ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C65/21C07C51/367
Inventor 谢智乾王哲烽益兵刘启皓钟静芬时惠麟
Owner SHANGHAI INST OF PHARMA IND CO LTD
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