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Environment-friendly synthetic method of 4-bromomethyl quinolinone

A bromomethylquinolinone, green synthesis technology, applied in the direction of organic chemistry and the like, can solve problems such as environmental pollution, and achieve the effects of good product quality, easy large-scale production and high production efficiency

Active Publication Date: 2016-07-13
陈科
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The usual process is to use concentrated sulfuric acid to carry out dehydration and ring-closure reaction to obtain the product (journal Medicinal Chemistry, 1988, 31 (10): 1910-18); after the reaction is completed, 4-bromomethylquinolinone is separated from the acid by water analysis , and then wash with a large amount of water to PH ≥ 6, and then dry the product. This method produces a large amount of waste sulfuric acid and low-concentration acidic water, which is easy to cause environmental pollution.

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0017] In a 5000L enamel reactor, after putting in 4000 kg of dichloroethane, 500 kg of acetoacetanilide bromide, and stir evenly; at the same time, put 1000 kg of dichloroethane and 1000 kg of dichloride into another 2000L reactor. Phosphorus, start to heat up the 5000L reactor and the 2000L reactor to the reflux of dichloroethane at the same time, and the reaction temperature is 83°C; The dichloroethane after the dehydration and distillation of the reactor is condensed and enters the 5000L reactor, and the distillation speed of the two reactors is controlled synchronously; after 12 hours of reaction, the temperature is lowered to normal temperature; the 4-bromomethylquinolinone is separated by a filter press, After this 4-bromomethylquinolinone is beaten and washed with dichloroethane, and then separated by a filter press, the obtained wet product containing dichloroethane solvent is vacuum-dried to obtain 442 kilograms of white powder Foam solid; yield 95.08%, purity 99.67%...

Embodiment 2

[0019] In a 5000L enamel reactor, after putting in 4000 kg of dichloroethane, 500 kg of acetoacetanilide bromide, and stir evenly; at the same time, put 1000 kg of dichloroethane and 1000 kg of dichloride into another 2000L reactor. Phosphorus, start to heat up the 5000L reactor and the 2000L reactor to the reflux of dichloroethane at the same time, and the reaction temperature is 83°C; The dichloroethane after the dehydration and distillation of the reactor is condensed and enters the 5000L reactor, and the distillation speed of the two reactors is controlled synchronously; after 24 hours of reaction, the temperature is lowered to normal temperature; the 4-bromomethylquinolinone is separated by a filter press, After this 4-bromomethylquinolinone was beaten and washed with dichloroethane, and then separated by a filter press, the obtained wet product containing dichloroethane solvent was vacuum-dried to obtain 436 kilograms of white powder Foam solid; yield 93.08%, purity 99.0...

Embodiment 3

[0021] In the 5000L enamel reaction kettle, after dropping 4000 kilograms of dichloromethane, 500 kilograms of acetoacetanilide bromide, after stirring evenly; simultaneously in another 2000L reaction kettle, drop 1000 kilograms of dichloromethane and 1000 kilograms of phosphorus pentoxide, At the same time, the temperature of the 5000L reactor and the 2000L reactor was raised to the reflux of dichloromethane, and the reaction temperature was 39°C; after 1 hour of reflux, the dichloromethane distilled from the 5000L reactor was condensed into the 2000L reactor, and the 2000L reactor was dehydrated and distilled The final dichloromethane enters the 5000L reactor after being condensed, and the distillation speed of the two reactors is controlled synchronously; after reacting for 36 hours, the temperature is lowered to normal temperature; After bromomethylquinolinone is beaten and washed with dichloroethane, and then separated by a filter press, the obtained wet product containing...

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Abstract

The invention discloses an environment-friendly synthetic method of 4-bromomethyl quinolinone. The environment-friendly synthetic method comprises the following steps: adding acetoacetanilide bromide as a raw material into an anhydrous organic solvent; taking out moisture generated in reaction by virtue of the organic solvent as a water carrier while heating, condensing the moisture-containing organic solvent, adding the organic solvent into a reaction kettle filled with phosphorus pentoxide, and carrying out dehydration under stirring; continuously distilling the organic solvent in the reaction kettle filled with phosphorus pentoxide, returning the distilled anhydrous organic solvent to an acetoacetanilide bromide reaction kettle as the water carrier, carrying out dehydration cyclization on acetoacetanilide bromide so as to generate 4-bromomethyl quinolinone, cooling the system to the room temperature, carrying out filter pressing by directly utilizing a filter press, washing by virtue of an organic solvent, and drying, so as to obtain the product. According to the environment-friendly synthetic method, the yield of reaches 95% or above, and the purity of 4-bromomethyl quinolinone is more than or equal to 99.5%; and the product quality is good, waste acid and wastewater are not generated, the production efficiency is high, the cost is low, and large-scale production is easily realized.

Description

technical field [0001] The invention relates to the field of chemical synthesis, in particular to a green synthesis method of 4-bromomethylquinolinone. Background technique [0002] 4-bromomethylquinolinone is an intermediate of the new anti-ulcer drug rebamipide (trade name: Mogustar), and 4-bromomethylquinolinone has a large market. The usual process is to use concentrated sulfuric acid to carry out dehydration and ring-closure reaction to obtain the product (journal Medicinal Chemistry, 1988, 31 (10): 1910-18); after the reaction is completed, 4-bromomethylquinolinone is separated from the acid by water analysis , and then wash with a large amount of water to pH ≥ 6, and then dry the product. This method produces a large amount of waste sulfuric acid and low-concentration acidic water, which is easy to cause environmental pollution. Contents of the invention [0003] The object of the present invention is to provide a kind of green synthetic method of 4-bromomethylquin...

Claims

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Application Information

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IPC IPC(8): C07D215/227
CPCC07D215/227
Inventor 陈科伍雄飞
Owner 陈科
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