离子液体中6-羟基-3,4-二氢-2(1H)-喹啉酮的合成

Synthesis of 6-Hydroxy-3,4-dihydro-2(1H)-quinolinone in Ionic Liquid

研究了离子液体[bmim]Cl-AlCl3催化4-甲氧基苯胺与丙烯酰氯反应一锅法合成6-羟基-3,4-二氢-2(1H)-喹啉酮,并用IR、1HNMR和元素分析对其结构进行确证。在[bmim]Cl-AlCl3介质中,4-甲氧基苯胺与丙烯酰氯发生酰化反应生成N-(4-甲氧基苯基)丙烯酰胺。而后在[bmim]Cl-AlCl3和酰化反应产生的HCl协同作用下,经过分子内Friedel-Crafts烷基化和脱甲基化反应,以89.6%的产率得到6-羟基-3,4-二氢-2(1H)-喹啉酮。离子液体[bmim]Cl-AlCl3作为催化剂和反应介质可以回收利用,重复使用5次目标产物的产率无明显降低。

6-Hydroxy-3,4-dihydro-2 （1H）-quinolinone was synthesized by one-pot reaction of 4- methoxyaniline with acryloyl chloride using [ bmim ] Cl-AlCl3 ionic liquid as catalyst, and its structure was characterized and confirmed by IR, elemental analysis and 1HNMR spectra. Firstly, N-（ 4- Methoxyphenyl） acrylamide was obtained by acylation of 4-methoxyaniline using acryloyl chloride in [ bmim] Cl-AlCl3. Secondly, with the synergistic catalysts of [ bmim ] Cl-AlCl3 and HCl produced by aeylation,6-hydroxy-3,4-dihydro-2 （1H）-quinolinone was produced with a yield of 89.6% through intramolecular Friedel-Crafts alkylation and demethylation of N-（4-methoxyphenyl）aerylamide. As a task-specific ionic liquid, [ bmim ] Cl-AlCl3 plays the role as catalyst as well as solvent. And it can be recycled and utilized for five more times without significant decrease in the yield of the target compound.