The synthetic method of 7-hydroxyquinoline-4-carboxylic acid

A technology of hydroxyquinoline and a synthesis method, applied in directions such as organic chemistry, can solve the problems of expensive chemical reagents, expensive raw materials, difficult to obtain, etc., and achieve the effects of simple synthesis route, low cost of raw materials, and easy amplification

Active Publication Date: 2022-04-12
SUZHOU KANGRUN PHARMA
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Problems solved by technology

[0004] In order to solve the problems existing in the prior art above, the object of the present invention is to provide a kind of synthetic method of 7-hydroxyquinoline-4-carboxylic acid, avoid the raw material of original synthetic route expensive and not easy to obtain, use comparatively expensive chemical reagents etc.

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  • The synthetic method of 7-hydroxyquinoline-4-carboxylic acid

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[0030] The present invention will be further described below in conjunction with specific examples, but the examples are only exemplary and do not constitute any limitation to the scope of the present invention. Those skilled in the art should understand that the details and forms of the technical solutions of the present invention can be modified or replaced without departing from the spirit and scope of the present invention, but these modifications and replacements all fall within the protection scope of the present invention.

[0031] The synthetic technique of 7-hydroxyquinoline-4-carboxylic acid of the present invention is to take 6-bromoisatin as raw material to obtain 7-bromoquinoline-2,4-carboxylic acid through reaction with pyruvic acid, and then react with nitrobenzene Obtain 7-bromoquinoline-4-carboxylic acid, react 7-bromoquinoline-4-carboxylic acid methyl ester with methanol, and react with NH2Boc to obtain 7-((tert-butoxycarbonyl)amino)quinoline-4-carboxylic acid...

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Abstract

The invention discloses a method for synthesizing 7-hydroxyquinoline-4-carboxylic acid, which uses 6-bromoisatin as a raw material to react with pyruvic acid to obtain 7-bromoquinoline-2,4-carboxylic acid, and Nitrobenzene reacts to obtain 7-bromoquinoline-4-carboxylic acid, then reacts 7-bromoquinoline-4-carboxylic acid methyl ester with methanol, and reacts with NH2Boc to obtain 7-((tert-butoxycarbonyl)amino)quinoline ‑4‑carboxylate methyl ester, remove amino protection in hydrochloric acid and methanol solution to obtain 7‑aminoquinoline‑4‑carboxylate methyl ester, diazotization reaction occurs in concentrated sulfuric acid to generate 7‑hydroxyquinoline‑4‑ Methyl carboxylate, and finally hydrolyzed in aqueous sodium hydroxide solution to obtain 7-hydroxyquinoline-4-carboxylic acid. The synthesis method uses 6-bromoisatin as a raw material, the synthetic route is simple, the process selection is reasonable, the raw material cost is low, the raw material is simple and easy to obtain, the operation and post-treatment are convenient, the total yield is high, no highly toxic reagent is used, and it is easy to scale up and can be used. for mass production.

Description

technical field [0001] The invention belongs to the technical field of synthesis of pharmaceutical intermediates, and in particular relates to a synthesis method of 7-hydroxyquinoline-4-carboxylic acid. Background technique [0002] 7-Hydroxyquinoline-4-carboxylic acid is a key pharmaceutical intermediate and has a wide range of applications in drug design. For example, it can be used as the key skeleton of aminoacyl indazole immunomodulators to treat autoimmune diseases. 7-Hydroxyquinoline-4-carboxylic acid is reduced to 7-hydroxy-1,2,3,4-tetrahydroquinoline-4-carboxylic acid, and then the carboxylic acid at position 4 is combined with tetrahydroindazole to form aminoacylindazole azoles; this kind of aminoacyl indazole immunomodulator has the effect of inhibiting blood coagulation factor FXIIa, by inhibiting FXIIa to generate high molecular weight kininogen (HK), to regulate immune cell chemotaxis, to achieve the effect of treating thrombosis and autoimmune diseases Purpo...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D215/50
CPCC07D215/50
Inventor 赵波徐卫良徐炜政
Owner SUZHOU KANGRUN PHARMA
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