Synthetic method of 4-amino-6-nitro-3-bromoquinoline

Through a simplified reaction of concentrated sulfuric acid and nitric acid, combined with alkalization treatment, the efficient synthesis of 4-amino-6-nitro-3-bromoquinoline was successfully achieved, solving the problems of complex preparation methods and high cost in the existing technology. Provides a simple path suitable for industrial production.

CN105461623AInactive Publication Date: 2016-04-06JIANGSU UNIV OF TECH
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Patent Information

Application Number
CN201511002475.5
Authority / Receiving Office
CN · China
Patent Type
Applications(China)
Current Assignee / Owner
Filing Date
2015-12-29
Publication Date
2016-04-06
Estimated Expiration
Not applicable · inactive patent

AI Technical Summary

Technical Problem

The existing preparation method of 4-amino-6-nitro-3-bromoquinoline is complex and costly. It lacks a simple and efficient synthesis route and is difficult to meet the needs of industrial production.

Method used

Using 4-amino-3-bromoquinoline as the starting material, through the reaction of concentrated sulfuric acid and excess concentrated nitric acid, combined with alkalinization treatment, and through filtration, washing and purification steps, 4-amino-6-nitro-sulfate is obtained , then refluxed in dimethyl sulfoxide and added acetone, and cooled to precipitate the pure product.

Benefits of technology

A simple synthesis route of 4-amino-6-nitro-3-bromoquinoline is realized. The reaction conditions are mild, the cost is low, it is suitable for industrial production, and the yield and product purity are improved.

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Abstract

The invention relates to 4-amino-6-nitro-3-bromoquinoline that is a precursor for preparing nociceptin antagonists. The invention discloses a synthetic method of 4-amino-6-nitro-3-bromoquinoline. The synthetic method comprises the following steps: carrying out iron powder reduction reaction on 4-nitroquinoline-N-oxide, as a raw material, in the presence of acetic acid, so as to generate 4-aminoquinoline; carrying out bromination reaction, so as to generate 4-amino-3-bromoquinoline; finally carrying out nitration reaction, so as to generate 4-amino-6-nitro-3-bromoquinoline. The compound structure of 4-amino-6-nitro-3-bromoquinoline is represented by 1H-NMR, 13C-NMR and IR. The adopted raw materials and reagents are cheap and easily available, the synthetic method is simple and feasible, and reaction conditions are mild; according to the synthetic method, a simple and convenient synthetic way is developed for the synthesis of 4-amino-6-nitro-3-bromoquinoline compounds.
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