离子液体中6-羟基-2(1H)-喹啉酮的合成

研究了对甲氧基苯胺经溴化、酰化和Heck反应在离子液体中合成6-羟基-2(1H)-喹啉酮的方法。对甲氧基苯胺与离子液体bmim]Br3发生选择性溴化反应,以98.2%的收率得到质量分数为99.5%的2-溴-4-甲氧基苯胺;2-溴-4-甲氧基苯胺与丙烯酰氯发生酰化反应,以95.7%的收率得到N-(2-溴-4-甲氧基苯基)丙烯酰胺;在离子液体、醋酸钯、碳酸钾和1,3-双(二苯基膦)丙烷反应体系中,N-(2-溴-4-甲氧基苯基)丙烯酰胺顺利地发生分子内Heck反应,以91.5%的收率得到6-羟基-2(1H)-喹啉酮。该方法原料易得,反应条件易控制,收率高,离子液体可以重复使用,对环境友好。

Synthesis of 6-Hydroxy-1H-quinolin-2-one in Ionic Liquid

A method for the synthesis of 6-hydroxy-1H-quinolin-2-one in ionic liquid was investigated.The title compound was prepared from p-methoxyaniline via bromination,acylation and the Heck reaction.The effects of reaction conditions on bromination and the Heck reaction were investigated.p-Methoxyaniline reacted with ionic liquid bmim]Br3 to give 2-bromo-4-methoxyaniline in 98.2% yield and 99.5% purity.N-(2-Bromo-4-methoxyphenyl)acrylamide was obtained by the acylation of 2-bromo-4-methoxyaniline with acryloyl chloride in 95.7% yield.The Heck reaction of N-(2-bromo-4-methoxyphenyl)acrylamide was effectively performed in the presence of ionic liquid bmim]Br,Pd(OAc)2,K2CO3 and DPPP to give 6-hydroxy-1H-quinolin-2-one in 91.5% yield.The new procedure for preparing 6-hydroxy-1H-quinolin-2-one has the advantages of good yield,simple operation and environmental benignity.