Yuan Jia-chen
2014
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Journal
Fine chemicals
Abstract
6-Hydroxy-3,4-dihydro-2( 1H)-quinolinone was synthesized by one-pot reaction of 4-methoxyaniline with acryloyl chloride using [bmim]Cl-AlCl3ionic liquid as catalyst,and its structure was characterized and confirmed by IR,elemental analysis and1HNMR 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-AlCl3and HCl produced by acylation,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) acrylamide. As a task-specific ionic liquid,[bmim]Cl-AlCl3plays 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.