Method for preparing N- formyl-2H-4chloroquinoline derivate

A -2H-4-, formyl technology, applied in the field of preparation of N-formyl-2H-4-chloroquinoline derivatives, can solve the problems of unsatisfactory yield, many side reactions, unfriendly environment and the like, and achieves The effect of simple operation, improved reaction yield, and easy availability of raw materials

Inactive Publication Date: 2011-06-29
ZHEJIANG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the reagent POCl used in this method 3 Unfriendly to the environment, and this kind of Vilsmeier reagent has strong activity, many side reactions, and the yield is not ideal

Method used

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  • Method for preparing N- formyl-2H-4chloroquinoline derivate
  • Method for preparing N- formyl-2H-4chloroquinoline derivate
  • Method for preparing N- formyl-2H-4chloroquinoline derivate

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] The preparation of embodiment 1N-formyl-4-chloro-2-phenyl-2H-quinoline

[0024] Add 0.66g N,N-dimethylformamide into a 50mL three-necked reaction flask equipped with a magnetic stirrer, a drying tube, a thermometer, and a dropping funnel, stir in an ice-water bath and cool down to 0-5°C, then add bis(tri Chloromethyl)carbonate solution (0.891g, 3mmol, dissolved in 3mL toluene), reacted at 0~5℃ for 45min after dropping, and then added dropwise at 0~5℃ containing 1-(2-aminobenzene)- The toluene solution of 3-phenylchalcone (0.224g, 1mmol, dissolved in 3mL toluene) was reacted at 0-5°C for 1 hour after dropping, and then heated to 90°C for 3 hours. The progress of the reaction was tracked by TLC. After the reaction, the reaction product was separated and purified: the above reaction mixture was poured into 15 g of crushed ice, and the pH value was adjusted to about 8 with 10% NaOH solution, and then stirred for 0.5 h to complete hydrolysis, then the organic layer was separ...

Embodiment 2

[0026] The preparation of embodiment 2N-formyl-4-chloro-2-phenyl-2H-quinoline

[0027] Add 0.54g N,N-dimethylformamide into a 50mL three-necked reaction flask equipped with a magnetic stirrer, a drying tube, a thermometer, and a dropping funnel, stir in an ice-water bath and cool down to 0-5°C, then dropwise add bis(tri Chloromethyl)carbonate solution (0.594g, 2mmol, dissolved in 2mL toluene), reacted at 0-5°C for 45min after dropping, then added dropwise at 0-5°C containing 1-(2-aminobenzene)- The toluene solution of 3-phenylchalcone (0.224g, 1mmol, dissolved in 3mL toluene) was reacted at 0-5°C for 2 hours after dropping, then heated to 90°C for 3 hours, followed by TLC. Aftertreatment is the same as in Example 1, and the yield is 56%. Physical property data is with embodiment 1.

Embodiment 3

[0028] The preparation of embodiment 3N-formyl-4-chloro-2-phenyl-2H-quinoline

[0029]Add 2.2g of N,N-dimethylformamide and 8mL of toluene into a 50mL three-necked reaction flask equipped with magnetic stirring, drying tube, thermometer, and dropping funnel, stir in an ice-water bath to cool down to 0-5°C, and then add dropwise Bis(trichloromethyl)carbonate solution (2.97g, 10mmol, dissolved in 6mL toluene), reacted at 0-5°C for 45min after dropping, then added dropwise at 0-5°C containing 1-(2-amino Benzene)-3-phenylchalcone toluene solution (0.224g, 1mmol, dissolved in 2mL toluene), reacted at 0-5°C for 2 hours after dropping, then raised the temperature to 90°C for 3 hours, followed by TLC schedule. Aftertreatment is the same as in Example 1, and the yield is 86%. Physical property data is with embodiment 1.

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Abstract

The invention discloses a preparation method for N-formyl-2H-4-chloroquinoline derivatives, which is characterized in that: the raw materials are bis(trichloromethyl) carbonate and N, N-dimethylformamide, and form a Vilsmeier reagent in organic solvent under the temperature of 0 to 5 DEG C; the temperature is controlled at 0 to 5 DEG C, and the substituted o-anisidine chalcone compound indicated in the structure formula (I) is added and reacts with the Vilsmeier reagent for 0.5 to 2 hours under the temperature of 0 to 5 DEG C; the temperature is increased to 80 to 100 DEG C, and the substituted o-anisidine chalcone compound and the Vilsmeier reagent react for 1 to 15 hours; after finishing the reaction, N-formyl-2H-4-chloroquinoline derivatives indicated in the structure formula (II) are obtained after the reaction products are separated and purified. The preparation method has the advantages of available raw materials, mild reaction condition, simple operation, high reaction yield, low pollution, and the like, which is a chemical synthetic method with good popularization and application prospect.

Description

(1) Technical field [0001] The invention relates to a preparation method of N-formyl-2H-4-chloroquinoline derivatives. (2) Technical background [0002] N-formyl-2H-4-chloroquinoline derivatives themselves have certain pharmacological activities and are important intermediates for the synthesis of quinoline drugs. [0003] The synthetic method of obtaining N-formyl-2H-4-chloroquinoline derivatives by one-step cyclization of substituted o-aminochalcones has few reports in the literature, and currently only POCl 3 / DMF synthesized Vilsmeier reagent and a series of substituted o-aminochalcones undergo ring closure reactions to obtain N-formyl-2H-4-chloroquinoline derivatives. However, the reagent POCl used in this method 3 It is not friendly to the environment, and this Vilsmeier reagent has strong activity, many side reactions, and the yield is not ideal. With the enhancement of people's awareness of environmental protection, more and more attention is paid to the green tre...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D215/18C07D409/04C07D407/04
Inventor 李振华郑存苏为科
Owner ZHEJIANG UNIV OF TECH
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