Synthetic process of 2-phenyl-6-hyroxy-3-pyridazone

doi:10.16085/j.issn.1000-6613.2017-0086

Abstract

Abstract: 2-phenyl-6-hydroxy-3-pyridazone is a kind of important heterocyclic compound which is an important activity medicine and pesticide intermediates. Phenylhydrazine hydrochloride was synthesized with aniline as raw material by diazotization, reduction reaction. Then, phenylhydrazine hydrochloride was reacted with maleic anhydride to get 2-phenyl-6-hyroxy-3-pyridazone. The effects of technical parameters on the yield of 2-phenyl-6-hyroxy-3-pyridazone were studied through single-factor experimental method, such as raw materials ratio, reaction time and reaction temperature, etc. The optima reaction conditions were determined as follow:n(C₆H₇N):n(NaNO₂):n(HCl)=1:1.02:2.3, reduction temperature 85℃, reduction time 2h, condensation temperature 100℃,condensation time 3h, the 85% yield of 2-phenyl-6-hyroxy-3-pyridazone could be reached. It show that synthetic is the target product.by melting,IR,NMR and HPLC characterization and analysis.

Key words: 2-phenyl-6-hyroxy-3-pyridazone, aniline, phenylhydrazine hydrochloride, maleic anhydride, diazotization reaction, condensation reaction

摘要： 2-苯基-6-羟基-3-哒嗪酮是一种重要杂环类化合物，是合成医药、农药重要的活性中间体。本文以苯胺为起始原料，经重氮化、还原等反应制得苯肼盐酸盐，再与顺丁烯二酸酐缩合得到2-苯基-6-羟基-3-哒嗪酮。通过单因素实验的方法研究了物料配比、反应时间及反应温度等因素对产物收率的影响，获得的最佳工艺条件为：n（苯胺）∶n（亚硝酸钠）∶n（浓盐酸）=1∶1.02∶2.3，还原反应温度85℃，还原反应时间2h，缩合反应温度100℃，缩合反应时间3h，此条件下合成2-苯基-6-羟基-3-哒嗪酮的收率达到85%，通过熔点测定、红外光谱、核磁共振氢谱和液相色谱测定表征和分析，表明合成物质确为目标产物。

关键词: 2-苯基-6-羟基-3-哒嗪酮, 苯胺, 苯肼盐酸盐, 顺丁烯二酸酐, 重氮化反应, 缩合反应

CLC Number:

TQ224.7

LIU Xinran, WANG Wenfeng, HU Yanfei, LU Yong, CHEN Tianyun. Synthetic process of 2-phenyl-6-hyroxy-3-pyridazone[J]. Chemical Industry and Engineering Progress, 2017, 36(S1): 398-401.

刘欣然, 王文峰, 胡燕飞, 陆勇, 陈天云. 2-苯基-6-羟基-3-哒嗪酮的合成工艺[J]. 化工进展, 2017, 36(S1): 398-401.

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