Synthesis method of 4-amino-2-hydroxy-3-isopropoxybenzoic acid

A technology of isopropoxybenzoic acid and synthesis method, applied in the direction of preparation of nitro compounds, chemical instruments and methods, preparation of carboxylate, etc., achieving the effects of high yield, simple operation and short route

Active Publication Date: 2020-08-21
阿里生物新材料(常州)有限公司
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  • Application Information

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Problems solved by technology

The synthetic method of 4-amino-2-hydroxyl-3-isopropoxybenzoic acid is rarely reported in the literature

Method used

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  • Synthesis method of 4-amino-2-hydroxy-3-isopropoxybenzoic acid

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preparation example Construction

[0036] A kind of synthetic method of 4-amino-2-hydroxyl-3-isopropoxybenzoic acid, this synthetic method comprises the steps:

[0037] (1) Under low temperature conditions, use dichloromethane as a solvent, pour raw materials A and triethylamine into the solvent and mix evenly, add acetyl chloride dropwise, after the dropwise addition, heat up, stir and react to obtain compound B; low temperature is -18~-3℃, the mass ratio of compound A, acetyl chloride and triethylamine is: 1.5~2.5:1:2~4, the solid-liquid g / mL ratio of compound A and dichloromethane is 1:12~14 ;

[0038] (2) Add compound B to dimethylformamide, lower the temperature, add sodium hydrogen, heat up, react, cool, add isopropyl bromide dropwise, after the dropwise addition, heat up and react to obtain compound C; compound B, sodium hydrogen, The mass ratio of isopropyl bromide is 6~7:2.5~3:4~5, and the solid-liquid g / mL ratio of compound B and dimethylformamide is 1:10~15; the preparation of compound C solution is...

Embodiment

[0044] (1) Add 46g of compound A, 61g of triethylamine and 600mL of dichloromethane into the reaction flask, add 32g of acetyl chloride dropwise in an ice-water bath, after the drop is complete, heat up to 2,3°C and stir for 2h, detect by TLC, the reaction of the raw materials is complete , adding saturated sodium bicarbonate (300 ml), extracting with dichloromethane (500 ml*2), concentrating the organic phase, and column chromatography (mobile phase: n-hexane / ethyl acetate=50 / 1) to obtain 42.3 g of colorless Transparent oil, namely compound B, with a purity of 95.5% and a yield of 70.48%;

[0045] (2) Add 65g of compound B and dimethylformamide to the reaction bottle, cool to 0°C, add 30g of sodium hydrogen, react at 22°C for 2h, re-cool to 0°C, add 45g of isopropyl bromide dropwise, dropwise , heated to 25°C and reacted for 16 hours, TLC detection, the reaction of the raw materials was completed, the reaction solution was poured into 1000 ml of ice water, 6M hydrochloric aci...

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Abstract

The invention belongs to a medical intermediate, and particularly relates to a synthesis method of 4-amino-2-hydroxy-3-isopropoxybenzoic acid. The synthesis method of the 4-amino-2-hydroxy-3-isopropoxybenzoic acid is provided for the first time, a synthesis route is provided for the synthesis method of the 4-amino-2-hydroxy-3-isopropoxybenzoic acid, the synthesis method is short in route, reasonable in design, easy to operate and easy to control, and meanwhile the yield of the obtained product is high.

Description

technical field [0001] The invention belongs to pharmaceutical intermediates, in particular to a method for synthesizing 4-amino-2-hydroxyl-3-isopropoxybenzoic acid. Background technique [0002] The synthetic method of compound 4-amino-2-hydroxyl-3-isopropoxybenzoic acid and related derivatives are widely used in medicinal chemistry and organic synthesis. The synthesis method of 4-amino-2-hydroxyl-3-isopropoxybenzoic acid is rarely reported in the literature. Therefore, it is necessary to develop a synthetic method that is easy to obtain raw materials, easy to operate, easy to control the reaction, suitable for overall yield, and suitable for industrial production. Contents of the invention [0003] Technical problem to be solved by the present invention: Aiming at the existing problems described above, a synthetic method of 4-amino-2-hydroxyl-3-isopropoxybenzoic acid is provided. [0004] In order to solve the problems of the technologies described above, the present i...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C227/04C07C229/64
CPCC07C227/04C07C201/12C07C201/08C07C67/29C07C67/14C07C229/64C07C205/59C07C205/44C07C69/16
Inventor 史建云王超许义波
Owner 阿里生物新材料(常州)有限公司
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