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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。
A method for the synthesis of 6-hydroxy-2 (1H) -quinolinone in p-methoxyaniline by bromination, acylation and Heck reaction was studied. Methoxyaniline and ionic liquid [bmim] Br3 selective bromination reaction to obtain 98.2% yield mass fraction of 99.5% 2-bromo-4-methoxyaniline; 2-bromo-4-methyl Acyloxyaniline was acylated with acryloyl chloride to give N- (2-bromo-4-methoxyphenyl) acrylamide in 95.7% yield; in the ionic liquid, palladium acetate, potassium carbonate and 1,3- The intramolecular Heck reaction of N- (2-bromo-4-methoxyphenyl) acrylamide smoothly occurred in the bis (diphenylphosphino) propane reaction system, yielding 6-hydroxy-2 1H) -quinolinone. The method is easy to obtain raw materials, easy to control the reaction conditions, high yield, ionic liquid can be reused, environmentally friendly.