A kind of method for preparing hydroxy-2(1h)-quinolinone

Abstract

The invention discloses a method for preparing hydroxyl-2(1H)-quinolinone, and belongs to the field of organic chemistry. The method comprises the following steps: enabling an aminophenylboric acid compound and trans-beta-aryl acryloyl chloride to react under the existence of triethylamine or pyridine so as to generate a trans-amide intermediate, and then carrying out temperature rising reaction in an organic solvent under the existence of aluminum chloride anhydrous and B(C6F5)3; cooling after completing the reaction, and adding hydrogen peroxide for oxidization, thus obtaining the hydroxyl-2(1H)-quinolinone. The method disclosed by the invention has the advantages that raw materials are easy to obtain, hydroxyl quinolinone products in different positions can be obtained through differentinitial raw materials, and an existing synthetic route is enriched.

Description

Technical field: [0001] The invention relates to a preparation method of hydroxy-2(1H)-quinolinone, which belongs to the technical field of organic chemistry. Background technique: [0002] Hydroxy-2(1H)-quinolinones have good biological activity, exhibit a variety of drug activities in different drug molecules, and are considered to be potential anti-tumor structures, so they have been widely used in medicine. Applications. 6-Hydroxy-2(1H)-quinolinone is an important intermediate in the synthesis of cilostazol for the treatment of stable intermittent claudication. 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, cerebral circulation drugs and herbicides; 7-hydroxy-2(1H)-quinolinone is An important intermediate for the synthesis of atypical antipsychotic aripiprazole, which has a completely different mechanism of action than typical and a...

AI Technical Summary

Problems solved by technology

[0004] (1) the nitro group of 2-nitrocinnamic acid that the benzene ring is substituted by hydroxyl is reduced to amino, and then carry out ring-forming reaction, because this method is subjected to the limitation of production cost, production equipment and production scale, is not suitable for industrialized large-scale production

[0005] (2) The target compound is synthesized by oxidation, acetylation, hydrolysis, and dealkoxylation of the quinoline compound whose benzene ring is substituted by hydroxyl or alkoxy group. Although the synthetic route is easy to operate, the total yield is only about 17%. , which limits its application, and the price of reaction raw materials is high, and the source of raw materials is limited

[0006] (3) Use methoxyaniline and acryloyl chloride as raw materials to synthesize hydroxy-2(1H)-quinolinone through bromination, acylation and intramolecular Heck reaction. This method requires expensive metal Pd catalysts to effectively Catalyzes the Heck reaction, limiting its economics

However, the use of a large excess of anhydrous aluminum trichloride catalyst system is difficult for post-treatment, and a large amount of waste water, waste residue and waste gas are produced during the reaction process, and the environmental pollution is relatively serious.

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