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Microwave-assisted synthesis of 2-(1H)-quinolinone compound

A microwave-assisted, quinolinone-based technology, applied in the direction of organic chemistry, can solve the problems of harsh reaction conditions, long reaction time, and low reaction yield, and achieve the effect of reducing reaction steps, simple operation, and high yield

Inactive Publication Date: 2018-09-07
HUNAN UNIV OF SCI & ENG +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] This type of reaction has the following disadvantages: it needs to synthesize and purify quinoline nitrogen oxide in advance, use excessive activator, the reaction time is long, and the reaction conditions are harsh
However, the reaction conditions of this reaction are harsh, the substrate is limited, and the reaction yield is low.

Method used

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  • Microwave-assisted synthesis of 2-(1H)-quinolinone compound
  • Microwave-assisted synthesis of 2-(1H)-quinolinone compound
  • Microwave-assisted synthesis of 2-(1H)-quinolinone compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0061] Embodiment 1: the preparation of 2-(1H)-quinolinone:

[0062] In a 50mL round bottom flask, 1.29g of quinoline, 1.23g of ethyl chloroacetate, 0.54g of distilled water, and 20ml of ethyl acetate were successively added, and the resulting mixture was subjected to microwave radiation reaction in a 300W microwave stirring reaction device for 25 minutes. The reaction solution was washed with hot water, separated, and the organic phase was collected. Ethyl acetate and ethyl chloroacetate were removed under reduced pressure, and 1.39 g of the corresponding 2-(1H)-quinolinone was obtained by recrystallization, with a yield of 96%.

Embodiment 2

[0063] Embodiment 2: the preparation of 3-methyl-2-(1H)-quinolinone

[0064] In a 50mL pressure-resistant reaction tube, 1.43g of 3-methylquinoline, 1.23g of ethyl chloroacetate, 0.54g of distilled water, and 20ml of ethyl acetate were sequentially added, and the resulting mixture was reacted by microwave radiation in a 300W microwave stirring reaction device for 25 minute. Wash the reaction solution with hot water, separate the liquids, collect the organic phase, remove ethyl acetate and ethyl chloroacetate under reduced pressure, and recrystallize to obtain 1.43 g of the corresponding 3-methyl-2-(1H)-quinolinone with a yield of 90 %.

Embodiment 3

[0065] Embodiment 3: Preparation of 4-methyl-2-(1H)-quinolinone

[0066] In a 50mL pressure-resistant reaction tube, 1.43g of 4-methylquinoline, 1.23g of ethyl chloroacetate, 0.54g of distilled water, and 20ml of ethyl acetate were sequentially added, and the resulting mixture was reacted by microwave radiation in a 300W microwave stirring reaction device for 25 minute. Wash the reaction solution with hot water, separate the liquids, collect the organic phase, remove ethyl acetate and ethyl chloroacetate under reduced pressure, and recrystallize to obtain 1.50 g of the corresponding 4-methyl-2-(1H)-quinolinone with a yield of 94 %.

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Abstract

The invention belongs to the field of synthesis of organic intermediates, and specifically discloses a microwave-assisted synthesis method of a 2-(1H)-quinolinone compound: an addition reaction of a quinoline raw material and water under the condition of a reaction accelerator and microwave assistance is performed to obtain the 2-(1H)-quinolinone compound; the quinoline raw material is quinoline or a quinoline derivative having a substituent at a position other than 2-site on a quinoline ring; the reaction accelerator is 2-chloroacetate and / or 2-bromoacetate. The method has the advantages ofsimple raw materials, simple reaction conditions, short reaction time, greenness, energy saving, high reaction selectivity and high yield, excellent compatibility of substrate functional groups, andhigh application value.

Description

technical field [0001] The invention belongs to the technical field of organic intermediate synthesis, and in particular relates to a synthesis method of 2-(1H)-quinolinone compounds. Background technique [0002] 2-(1H)-Quinolinone and its derivatives are a class of important heterocyclic compounds containing quinoline ring structural units, which widely exist in various natural products, and are also an important class of organic synthesis intermediates and drug molecules , has a wide range of application values ​​in the fields of medicine and materials. At present, a variety of drugs containing this structural unit have been listed, such as the anti-ulcer drug rebamipide [BIO Clinica, 2012, 27 (4): 365-370], tipifarnib [Curr.Top.Med.Chem. , 2003, 3(10): 105-102.], indacaterol, etc. [0003] At present, there have been a large number of reports on the synthesis of 2-(1H)-quinolinone compounds, including: Tetrahedron Lett.1998, 39, 9839-9840; Org. Lett.2014, 16, 3568-3571...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D215/227C07D215/48
CPCC07D215/227C07D215/48
Inventor 何卫民曹忠卢玲慧彭莎何卫保曾飞包文虎王毅
Owner HUNAN UNIV OF SCI & ENG