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Preparation method of 6,7-dimethyl-4-hydroxyquinoline

A technology of hydroxyquinoline and dimethylphenyl, which is applied in the field of novel preparation of pharmaceutical intermediates and can solve problems such as difficulty in synthesis

Inactive Publication Date: 2017-10-24
湖南华腾制药有限公司
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The synthesis of 6,7-dimethyl-4-hydroxyquinoline is difficult at present

Method used

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  • Preparation method of 6,7-dimethyl-4-hydroxyquinoline
  • Preparation method of 6,7-dimethyl-4-hydroxyquinoline
  • Preparation method of 6,7-dimethyl-4-hydroxyquinoline

Examples

Experimental program
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Embodiment 1

[0019] (1) Synthesis of 1-(4,5-dimethyl-2-nitrophenyl)ethanone

[0020] Add 29g of 1-(3,4-dimethylphenyl)ethanone to 260ml of acetic acid, add 62g of concentrated nitric acid, stir overnight at room temperature, concentrate, then add ethyl acetate and water, separate, dry, concentrate, and the residue 31 g of 1-(4,5-dimethyl-2-nitrophenyl)ethanone was obtained by column separation.

[0021] (2) Synthesis of 1-(2-amino-4,5-dimethylphenyl)ethanone

[0022] Add 30g of 1-(4,5-dimethyl-2-nitrophenyl)ethanone to 240ml of anhydrous methanol, then add 4g of 10% palladium carbon, pass in hydrogen, stir at room temperature for 4 hours, filter, and collect The filtrate was concentrated to obtain 22 g of 1-(2-amino-4,5-dimethylphenyl)ethanone.

[0023] (3) Synthesis of 6,7-dimethyl-4-hydroxyquinoline

[0024] Add 12g of sodium to 230ml of absolute ethanol, then 20g of (7-methyl-imidazo[1,2-a]pyridin-2-yl)methanol and 32g of ethyl formate, heat and reflux and stir for 9 hours, concentra...

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Abstract

The invention discloses a preparation method of 6,7-dimethyl-4-hydroxyquinoline. A target product is prepared by taking 1-(3,4-dimethyl phenyl)ethanone as a starting raw material through nitration, reduction and ring closing. The compound is an important medicine intermediate.

Description

technical field [0001] The invention relates to a novel preparation method of a pharmaceutical intermediate, in particular to a preparation method of 6,7-dimethyl-4-hydroxyquinoline. technical background [0002] Compound 6,7-dimethyl-4-hydroxyquinoline, the structural formula is: [0003] [0004] The compound 6,7-dimethyl-4-hydroxyquinoline and related derivatives are widely used in medicinal chemistry and organic synthesis. Currently, the synthesis of 6,7-dimethyl-4-hydroxyquinoline is difficult. Therefore, it is necessary to develop a synthetic method with easy-to-obtain raw materials, convenient operation, easy-to-control reaction and suitable overall yield. Contents of the invention [0005] The invention discloses a method for preparing 6,7-dimethyl-4-hydroxyquinoline, which uses 1-(3,4-dimethylphenyl)ethanone as a starting material, and undergoes nitration, reduction, close ring to obtain the target product 4, the synthesis steps are as follows: [0006] (1)...

Claims

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Application Information

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IPC IPC(8): C07D215/233
CPCC07D215/233
Inventor 不公告发明人
Owner 湖南华腾制药有限公司
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