5-((3-(3-Pyrrolidin-1-ylpropoxy)-4-methoxyanilino)methylene)-2,2-dimethyl-1,3-dioxane-4,6-dione → 6-methoxy-7-[3-(1-pyrrolidyl)propyloxy]-4(1H)-quinolinone

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Reaction Steps

After refluxing a solution of 5-((3-(3-pyrrolidin-1-ylpropoxy)-4-methoxyanilino)methylene)-2,2-dimethyl-1,3-dioxane-4,6-dione (4.9 g, 12 mmol) in phenyl ether (50 ml) for 1 minute, the mixture was poured into petroleum ether (500 ml). The solid was collected by filtration and purified by reverse phase chromatography on a Diaion (trade mark of Mitsubishi) HP20SS resin column eluting with water/methanol (100/0 increasing to 20/80). After removal of the solvent by evaporation, the purified product was azeotroped with a mixture of ethanol and toluene to give 6-methoxy-7-(3-pyrrolidin-1-ylpropoxy)-1,4-dihydroquinolin-4-one (1 g, 27%).

Provenance & Evidence