Synthesis method of 7-amino-5-bromoquinoline

A synthesis method and technology of bromoquinoline, applied in directions such as organic chemistry, can solve the problem of not synthesizing 7-amino-5-bromoquinoline and the like, and achieve the effects of simple synthesis route, low cost of raw materials, and reasonable process selection

Active Publication Date: 2021-03-30
SUZHOU KANGRUN PHARMA
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  • Abstract
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  • Application Information

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Problems solved by technology

However, there is no existing method for synthesizing 7-amino-5-bromoquinoline

Method used

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  • Synthesis method of 7-amino-5-bromoquinoline

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Embodiment Construction

[0019] 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.

[0020] The invention provides a synthesis process of 7-amino-5-bromoquinoline, which uses 7-nitro-1,2,3,4-tetrahydroquinoline as raw material to obtain 5-bromo-7-quinoline through bromination reaction. Nitro 1,2,3,4-tetrahydroquinoline, react with DDQ dehydrogenation to obtain 5-bromo-7-nitroquinoline, obtain 7-amino-5-bromoquinoline through reduction reaction of iron powder, the reaction style such as figure 1 As shown, the specific synthesis step...

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Abstract

The invention discloses a synthesis method of 7-amino-5-bromoquinoline, which comprises the following steps: carrying out a bromination reaction on 7-nitro-1, 2, 3, 4-tetrahydroquinoline serving as araw material to obtain 5-bromine-7-nitro-1, 2, 3, 4-tetrahydroquinoline, carrying out a dehydrogenation reaction on the 5-bromine- 7-nitro 1, 2, 3, 4-tetrahydroquinoline and DDQ to obtain 5-bromine-7-nitro quinoline, and carrying out iron powder reduction reaction to obtain 7-amino-5-bromoquinoline. The method provides a new synthetic route for synthesis of 7-amino-5-bromoquinoline, and the synthetic route is simple, reasonable in process selection, low in raw material cost, simple and easily available in raw materials, convenient to operate and post-treat, high in total yield, free of highlytoxic reagents, easy to amplify and suitable for 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 7-amino-5-bromoquinoline. Background technique [0002] 7-amino-5-bromoquinoline is an important pharmaceutical intermediate. Because of its unique properties, 7-amino-5-bromoquinoline is widely used in drug design. Michael G. Kelly et al developed benzamide derivatives as capsaicin receptor (VR) inhibitors for the treatment, prevention or amelioration of pain not limited to various origins or etiologies, such as acute, chronic, inflammatory and neuropathic pain , dental pain, and headaches (such as migraines, cluster headaches, and tension headaches). Compared with other VR-1 inhibitors, this new class of VR-1 inhibitors has the characteristics of low toxicity, good absorption, good half-life, good solubility, low protein binding, strong affinity, and few drug interactions. 7-amino-5-bromoquinoline is used as...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D215/38
CPCC07D215/38
Inventor 赵丽芳徐卫良徐炜政
Owner SUZHOU KANGRUN PHARMA
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