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The synthetic method of 6-(trifluoromethyl)quinoline-8-carboxylic acid

A technology of trifluoromethyl and synthesis method, which is applied in the field of synthesis of pharmaceutical intermediates, can solve the problems of low reagent safety and complicated operation, and achieve the effects of convenient operation and post-processing, simple raw materials, and low raw material cost

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

[0004] The purpose of the present invention is to provide a synthetic method of 6-(trifluoromethyl)quinoline-8-carboxylic acid, which avoids the disadvantages of low reagent safety and complicated operation in the existing synthetic route, and is easy to produce in large quantities

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  • The synthetic method of 6-(trifluoromethyl)quinoline-8-carboxylic acid

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Embodiment Construction

[0023] 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.

[0024] Among the present invention, the synthesis technique of 6-(trifluoromethyl)quinoline-8-carboxylic acid is to obtain 8-bromo-6-( Trifluoromethyl)quinoline, under pressure of carbon monoxide to give methyl 6-(trifluoromethyl)quinoline-8-carboxylate, finally hydrolyzed in aqueous lithium hydroxide to give 6-(trifluoromethyl) Quinoline-8-carboxylic acid, the reaction formula is as figure 1 shown.

[0025] The first step: the synthesis of 8-bro...

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Abstract

The invention discloses a synthesis method of 6-(trifluoromethyl)quinoline-8-carboxylic acid, which uses 2-bromo-4-(trifluoromethyl)aniline as raw material to obtain 8-bromo ‑6‑(trifluoromethyl)quinoline, 6‑(trifluoromethyl)quinoline‑8‑carboxylate methyl ester is obtained under pressure of carbon monoxide, and finally hydrolyzed in aqueous lithium hydroxide solution to obtain 6‑(trifluoromethyl) fluoromethyl) quinoline‑8‑carboxylic acid. The synthesis method of the invention has simple synthesis route, reasonable process selection, low raw material cost, simple and easy to obtain raw material, convenient operation and post-treatment, high total yield, easy scale-up and large-scale 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 6-(trifluoromethyl)quinoline-8-carboxylic acid. Background technique [0002] 6-(Trifluoromethyl)quinoline-8-carboxylic acid is widely used in drug design as a pharmaceutical intermediate of Guan Yu. For example, the 8-carboxyl group of 6-(trifluoromethyl)quinoline-8-carboxylic acid is structurally modified by 4-phenylpiperidine-4-methanol to generate NK-1 receptor antagonists for inhibiting NK-1 Receptors and serotonin reuptake. In recent years, it has been found that NK-1 antagonists can regulate 5-HT function through the noradrenergic pathway, and have been shown to weaken the function of presynaptic 5-HT receptors. Inhibition of these receptors has been associated with efficacy in mood disorders such as anxiety, depression, obsessive-compulsive disorder, binge eating disorder, and panic disorder. NK-1 anta...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D215/48
CPCC07D215/48
Inventor 赵波徐卫良徐炜政
Owner SUZHOU KANGRUN PHARMA
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