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Preparation method of 6-hydroxy-3,4-dihydro-2(1H)quinolinone

A technology of quinolinone and dihydro, which is applied in the field of chemical intermediate preparation, can solve the problems of low hydrolysis reaction yield of alkoxy compounds, difficult cyclization reaction, and inconspicuous effect, achieving mild reaction conditions and increasing yield , cost reduction effect

Inactive Publication Date: 2019-05-28
PANJIN GELIN KAIMO TECH CO LTD
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Problems solved by technology

[0003] The synthesis method reported in the literature is generally to react with p-alkoxyaniline and 3-chloropropionyl chloride, and the N2(4'-alkoxyphenyl)-3-chloropropionamide obtained is obtained through cyclization and then hydrolysis, but The hydrolysis reaction yield of alkoxy compounds is extremely low; or the N-(4'-hydroxyphenyl)-3-chloropropionamide prepared from p-hydroxyaniline is obtained by cyclization under the action of AlCl3, but according to this The method is difficult to carry out the cyclization reaction, try to use nitrobenzene as the solvent, the effect is not obvious

Method used

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Embodiment 1

[0013] A new synthetic method of 6-hydroxyl-3,4-dihydro-2 (1H) quinolinone, the synthetic method comprises the steps:

[0014] Dissolve 95g of aniline in 200mL of acetone, stir, cool down in an ice-salt bath to 0-5°C, slowly add 55mL of 3-chloropropionyl chloride dropwise with a dropping funnel, drop it for 0.5h, remove the ice bath; continue to stir at room temperature for 4h, react After completion, pour 400mL of 5% dilute hydrochloric acid into the reaction solution, a large amount of white solids precipitated out, stirred evenly, and suction filtered after cooling, the filter cake was washed with dilute hydrochloric acid (5%), then washed with water, and 89.5g of product N was obtained after drying. -Phenyl-3-chloropropanamide (I), the mother liquor was adjusted to pH=12 with dilute alkali, and CHCl 3 Unreacted aniline was recovered by extraction; yield 93%, m.p.119-120°C; 55g compound I and 116g AlCl 3 Put it into a reaction bottle, heat up to 150°C, react for 4 hours, t...

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Abstract

The invention belongs to the field of preparation of intermediates in chemical engineering, and particularly relates to a preparation method of 6-hydroxy-3,4-dihydro-2(1H)quinolinone. The preparationmethod comprises the following steps of using aniline and 3-chloropropionyl chloride as raw materials; performing cyclization, nitrification, reduction and diazotization hydrolysis, so as to synthesize the target product, namely 6-hydroxy-3,4-dihydro-2(1H)quinolinone. The preparation method has the advantages that the reaction conditions are mild, the cost is reduced, and the yield rate is increased.

Description

technical field [0001] The invention belongs to the field of preparation of chemical intermediates, and in particular relates to a preparation method of 6-hydroxy-3,4-dihydro-2(1H)quinolinone. Background technique [0002] A preparation method of 6-hydroxy-3,4-dihydro-2 (1H) quinolinone is an important intermediate for the synthesis of cilostazol (cilostazol, the trade name is pletal), and is used for the treatment of stable intermittent claudication (Clinical manifestations and typical symptoms of occlusive peripheral atherosclerosis). At the same time, it is also an important intermediate for the synthesis of antithrombotic drugs, antithrombinase, anti-inflammatory drugs, ulcer drugs, asthma drugs, cardiotonic drugs, drugs for treating cerebral circulation and herbicides, so it has been widely used in medicine. [0003] The synthesis method reported in the literature is generally to react with p-alkoxyaniline and 3-chloropropionyl chloride, and the N2(4'-alkoxyphenyl)-3-c...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D215/22
Inventor 宫宁瑞
Owner PANJIN GELIN KAIMO TECH CO LTD
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