Doebner-Miller法合成8-羟基喹哪啶的工艺研究

摘要

8-Hydroxyquinaldine,an important medicine intermediate,was synthesized by DoebnerMiller method from o-aminophenol,o-nitrophenol,crotonaldehyde,acetic acid and AlCl3 in the HCl aqueous solution under the optimal conditions:n(o-aminophenol) ∶ n(o-nitrophenol) ∶ n(crotonaldehyde) ∶ n(acetic acid) ∶ n(AlCl3)＝1 ∶ 0.3 ∶ 1.1 ∶ 1.0 ∶ 0.15,stirring speed was 400 r/min,drop time of crotonaldehyde was 3 h,and reaction carry out was at 90-100 ℃ for 5 h.The yield and purity of 8-hydroxyquinaldine were 76 ％ (calculated based on o-aminophenol added) and 99.3％ respectively after neutralization and distillation.The structure of 8-hydroxyquinaldine was confirmed by elemental analysis,IR,and 1H NMR.%以邻氨基苯酚、邻硝基苯酚和巴豆醛为原料,在含有乙酸的盐酸水溶液中,用Doebner-Miller法合成重要医药中间体8-羟基喹哪啶.较佳的反应条件为:n(邻氨基酚)∶n(邻硝基酚)∶n(巴豆醛)∶n(乙酸)∶n(AlCl3)＝ 1∶0.36∶1.1∶1.0∶0.15,搅拌速率为400 r/min,巴豆醛滴加时间为3h,在90～100℃反应5h,经中和、蒸馏等后处理得到8-羟基喹哪啶,收率76％(以邻氨基苯酚计),纯度99.3％.通过元素分析、红外光谱、核磁共振谱等对8-羟基喹哪啶的结构进行了表征.