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Synthesis method of 3-aminoquinoline-5-carboxylic acid methyl ester

A technology of aminoquinoline and methyl carboxylate, applied in the direction of organic chemistry, can solve the problems of m-chloroperoxybenzoic acid being explosive, difficult to use on a large scale, complicated route, etc. The effect of high yield

Active Publication Date: 2020-12-29
SUZHOU KANGRUN PHARMA
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Problems solved by technology

However, the experimental route is complicated, and two products are generated in the first step, resulting in a low yield; at the same time, m-chloroperoxybenzoic acid is explosive and dangerous, and is not easy to be used on a large scale

Method used

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  • Synthesis method of 3-aminoquinoline-5-carboxylic acid methyl ester

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Embodiment Construction

[0018] 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.

[0019] The synthetic technique of 3-aminoquinoline-5-methyl carboxylate of the present invention is to carry out bromination reaction with bromine to obtain 3-amino-5-bromoquinoline with 3-aminoquinoline as raw material, then through carbonyl insertion reaction Obtain 3-aminoquinoline-5-carboxylic acid methyl ester, its reaction formula is as follows:

[0020] .

[0021] The specific synthesis steps are as follows:

[0022] The first step: the s...

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Abstract

The invention discloses a synthesis method of 3-aminoquinoline-5-carboxylic acid methyl ester. The method comprises the following steps: carrying out a bromination reaction on 3-aminoquinoline servingas a raw material and bromine to obtain 3-amino-5-bromoquinoline, and carrying out a carbonyl insertion reaction to obtain the 3-aminoquinoline-5-carboxylic acid methyl ester. The method is simple insynthetic route, reasonable in process selection, simple and easily available in raw materials, convenient to operate and post-treat, relatively high in total yield and easy to amplify, and can be used for large-scale production.

Description

technical field [0001] The invention belongs to the technical field of synthesis of pharmaceutical intermediates, in particular to a synthesis method of methyl 3-aminoquinoline-5-carboxylate. Background technique [0002] 3-Aminoquinoline-5-carboxylic acid methyl ester is an important pharmaceutical intermediate. As a compound mainly composed of quinoline, it has been used in the research of anti-tumor drugs. The amino group at the 3-position of the compound is a high The active substitution site can be substituted by other groups to improve the biological activity of the compound, and the 5-position ester group can also react with some intermediates or fragments to obtain amide derivatives. The amide group is easy to bind to the receptor. Has good biological activity. Due to the superior properties of 3-aminoquinoline-5-carboxylic acid methyl ester, it has attracted extensive attention in the field of organic synthesis, especially in the field of medicinal chemistry. Blom...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D215/48
CPCC07D215/48
Inventor 赵丽芳徐卫良徐炜政
Owner SUZHOU KANGRUN PHARMA
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