离子液体中6-羟基-2(1H)-喹啉酮的合成研究
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TQ224.7, O621.3

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淮安市科技支撑项目(编号09010)


Study on Synthesis of 6-Hydroxy-1H-quinolin-2-one in Ionic Liquid
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    摘要:

    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,反应条件易于控制,反应收率高,离子液体可以重复使用,对环境友好。

    Abstract:

    A method for synthesis of 6-hydroxy-1H-quinolin-2-one in ionic liquid was studied. The title compound was prepared from p-methoxyaniline via bromination, acylation and Heck reaction. The effects of reaction conditions on bromination and Heck reaction were investigated. p-Methoxyaniline was reacted with ionic liquid [bmim]Br3 to afford 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 afford 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.

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袁加程.离子液体中6-羟基-2(1H)-喹啉酮的合成研究[J].精细化工,2010,27(6):

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  • 收稿日期:2010-02-03
  • 最后修改日期:2010-03-15
  • 录用日期:2010-03-16
  • 在线发布日期: 2010-05-13
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