Preparation method of 3-chloro(bromo)-6-nitroisoquinoline

A technology of nitroisoquinoline and nitrobenzoic acid, which is applied in the field of preparation of 3-chloro-6-nitroisoquinoline, can solve problems such as inability to promote
CN105017152AActive Publication Date: 2015-11-04烟台宁远药业有限公司
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Patent Information

Authority / Receiving Office
CN · China
Patent Type
Applications(China)
Current Assignee / Owner
烟台宁远药业有限公司
Publication Date
2015-11-04

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Abstract

The invention relates to a preparation method of 3-chloro(bromo)-6-nitroisoquinoline. The preparation method comprises that 2-chloro-4-nitrobenzoic acid as a raw material undergoes a nucleophilic substitution reaction to produce 2-(2-methoxy-2-oxoethyl)-4-nitrobenzoic acid, the 2-(2-methoxy-2-oxoethyl)-4-nitrobenzoic acid is hydrolyzed to form 2-(carboxymethyl)-4-nitrobenzoic acid, the 2-(carboxymethyl)-4-nitrobenzoic acid, acetyl chloride and ammonium hydroxide undergo a reaction to produce 2-(2-amino-2-oxoethyl)-4-nitrobenzoic acid, the 2-(2-amino-2-oxoethyl)-4-nitrobenzoic acid undergoes a cyclization reaction to produce 6-nitroisoquinolin-1,3(2H,4H)-dione, the 6-nitroisoquinolin-1,3(2H,4H)-dione undergoes a chlorination (bromination) reaction to produce 1,3-dichloro(bromo)-6-nitroisoquinoline, because of activity of isoquinoline at the first site, chlorine(bromine) at the first site is replaced by methoxybenzylamine so that 3-chloro(bromo)-N-(4-methoxybenzyl)-6-nitroisoquinolin-1-amine is formed, the p-methoxybenzyl group is removed by trifluoroacetic acid so that 3-chloro(bromo)-6-nitroisoquinolin-1-amine is formed, 1-amine is subjected to diazotization, and the hydrogen produced by diazotization is removed by heating so that a product is obtained. The preparation method is convenient for operation and has a high yield in each process.
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Description

technical field

[0001] The invention belongs to the field of pharmaceutical intermediates, in particular to a preparation method of 3-chloro(bromo)-6-nitroisoquinoline. Background technique

[0002] Isoquinoline and its derivatives are an important class of alkaloids with important biological activities, widely used in medicine, pesticides and other fields, so the synthesis of isoquinoline derivatives has received extensive attention.

[0003] The structural formula of isoquinoline:

[0004]

[0005] Derivatives of isoquinoline have a wide range of applications, especially in pharmaceutical intermediates. The literature has reported the synthetic method of 3-chloro-5-nitroisoquinoline, and its method is: use 1,3-dichloroisoquinoline to hydrogenate to obtain 3-chloroisoquinoline, and 3-chloroisoquinoline to obtain 3-Chloro-5-nitroisoquinoline. Due to the properties of isoquinoline molecules, this method cannot be extended to the synthesis of other similar structures. ...

Claims

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