Synthesis method of 8-bromine-4-carboxyl quinoline

A technology of carboxyquinoline and synthesis method, applied in the direction of organic chemistry and the like, can solve the problems of low synthesis yield, low reaction yield, high product price and the like, and achieves high synthesis yield, high selectivity and simple synthesis steps. Effect

Inactive Publication Date: 2013-12-25
CHEMFUTURE PHARMATECH JIANGSU
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0002] 8-Bromo-4-carboxyquinoline is an important pharmaceutical synthetic intermediate. The reaction route for synthesizing this compound is very long, and the final reaction yield is low, resulting in expensive products, which are not suitable for large-scale industrial production.
Existing literature provides the synthetic method that takes 7-bromoindolindione as raw material synthetic 8-bromo-4-carboxyquinoline, and this method synthetic yield is low, and raw material price is expensive, and reaction easily generates other by-products, does not need Helps reduce synthesis costs

Method used

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  • Synthesis method of 8-bromine-4-carboxyl quinoline
  • Synthesis method of 8-bromine-4-carboxyl quinoline

Examples

Experimental program
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Effect test

Embodiment 1

[0023] (1) Dissolve 50g of o-bromoaniline and 156.75g of ferric chloride hexahydrate in 750ml of glacial acetic acid, heat to 60°C, add 21.35g of butenone dropwise, and reflux (115°C) for 4 hours after the dropwise addition. Suction filter the reaction solution, wash the filter cake 3 times with dichloromethane, spin dry the filtrate, dissolve the solid obtained after spinning, adjust to alkaline with aqueous sodium hydroxide solution, then extract with dichloromethane, and combine the organic phases , dried over anhydrous sodium sulfate, filtered with suction, evaporated dichloromethane under reduced pressure, and passed the obtained crude product through a silica gel column with an eluent (petroleum ether: ethyl acetate = 40:1 V / V) to obtain a white solid 8 -Bromo-4-methylquinoline (2) 44g, yield 60%.

[0024] (2) Take 44g of the product 8-bromo-4-methylquinoline obtained in step (1) and add it to a three-necked flask, add 340ml of xylene and heat to reflux until dissolved, ...

Embodiment 2

[0027] (1) Dissolve 5g of o-bromoaniline and 11.77g of ferric trichloride hexahydrate in 75ml of glacial acetic acid, heat to 60°C, add 2.1g of butenone dropwise, and reflux (115°C) for 4 hours after the dropwise addition. Suction filter the reaction solution, wash the filter cake 3 times with dichloromethane, spin dry the filtrate, dissolve the solid obtained after spinning, adjust to alkaline with aqueous sodium hydroxide solution, then extract with dichloromethane, and combine the organic phases , dried over anhydrous sodium sulfate, filtered with suction, evaporated dichloromethane under reduced pressure, and passed the obtained crude product through a silica gel column with an eluent (petroleum ether: ethyl acetate = 40:1 V / V) to obtain a white solid 8 -Bromo-4-methylquinoline 3.74g, yield 58%.

[0028] (2) Take 3.74g of the product 8-bromo-4-methylquinoline obtained in step (1) and add it to a three-necked flask, add 35ml of xylene and heat to reflux until dissolved. Tak...

Embodiment 3

[0031] (1) Dissolve 5g of o-bromoaniline and 19.6g of ferric chloride hexahydrate in 75ml of glacial acetic acid, heat to 60°C, add 2.1g of butenone dropwise, and reflux (115°C) for 4 hours after the dropwise addition. Suction filter the reaction solution, wash the filter cake 3 times with dichloromethane, spin dry the filtrate, dissolve the solid obtained after spinning, adjust to alkaline with aqueous sodium hydroxide solution, then extract with dichloromethane, and combine the organic phases , dried over anhydrous sodium sulfate, filtered with suction, evaporated dichloromethane under reduced pressure, and passed the obtained crude product through a silica gel column with an eluent (petroleum ether: ethyl acetate = 40:1 V / V) to obtain a white solid 8 -Bromo-4-methylquinoline 3.6g, yield 56%.

[0032] (2) Add 3.6g of the product 8-bromo-4-methylquinoline obtained in step (1) into a three-necked flask, add 35ml of xylene and heat to reflux until dissolved, and take 3.6g of Se...

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Abstract

The invention discloses a synthesis method of 8-bromine-4-carboxyl quinoline, which comprises the following steps of (1) allowing bromoaniline to react with methyl vinyl ketone to form 8-bromine-4-methyl quinoline under the catalysis of ferric trichloride, (2) oxidizing 8-bromine-4-methyl quinoline with selenium dioxide in an organic solvent to form 8-bromoquinoline-4-methanal, and (3) oxidizing 8-bromoquinoline-4-methanal with hydrogen peroxide in an acid medium to form 8-bromine-4-carboxyl quinoline. The method takes cheaper bromoaniline as a raw material, and is simple in synthesis step, high in synthesis yield and high in selectivity.

Description

Technical field [0001] The invention is the field of pharmaceutical synthesis, which specifically involves a synthesis method of 8-bromo-4-carboxyloline. Background technique [0002] 8-bromo-4-carboxyl pyrine is an important pharmaceutical synthetic intermediate. It has a long reaction route that has synthesized the compound, and the final reaction yield is low, resulting in expensive product prices and not suitable for large-scale industrialized production.The existing literature provides a synthesis method for synthesizing 8-bromine-4-carboxyloline pyrinoline with 7-bromodramidonetus. This method is low in synthesis and expensive raw materials.It is conducive to reducing synthetic costs. Invention content [0003] The purpose of the present invention is to provide a synthesis method of 8-bromo-4-carboxyloline of carrion-4-carboxyloline with low cost and high yield. [0004] The technical solution used by the present invention to achieve the above purpose is as follows: [000...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D215/50
Inventor 徐骏吴妤萱
Owner CHEMFUTURE PHARMATECH JIANGSU
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