Synthesis of 6-(3-Aminophenyl)-4,5-dihydropyridazin-3(2H)-one

doi:10.3724/SP.J.1095.2014.30635

Chinese Journal of Applied Chemistry

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Synthesis of 6-(3-Aminophenyl)-4,5-dihydropyridazin-3(2H)-one

JIANG Liuping, KANG Congmin, LV Yingtao^*

(College of Chemical Engineering,Qingdao University of Science and Technology,Qingdao 266042,China)

Received:2013-12-12 Revised:2014-02-26 Published:2014-09-04 Online:2014-09-04

Abstract

Abstract: 6-(3-Aminophenyl)-4,5-dihydropyridazin-3(2H)-one(1) has been synthesized by using benzene and succinic anhydride as starting materials via a three-step process including Friedel-Crafts acylation, nitration, reduction with hydrazine hydrate in an overall yield of 58.3%. Under catalysis of Raney Ni, β-m-nitrobenzoylpropionic acid(3) reacted with hydrazine hydrate to give compound 1 by one step of nitro reduction and ring closing. The effects of the amount of hydrazine and reaction time on the yield of above reaction have been explored. When the reaction was refluxed for 4 h with molar ratio of hydrazine to compound 3 at 11.7∶1, the yield of compound 1 was up to 82.7%.

Key words: (aminophenyl)-dihydropyridazin-3(2H)-one, Raney Ni, hydrazine hydrate

CLC Number:

O626.4

JIANG Liuping, KANG Congmin, LV Yingtao*. Synthesis of 6-(3-Aminophenyl)-4,5-dihydropyridazin-3(2H)-one[J]. Chinese Journal of Applied Chemistry, DOI: 10.3724/SP.J.1095.2014.30635.

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Synthesis of 6-(3-Aminophenyl)-4,5-dihydropyridazin-3(2H)-one

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