Water → 4-hydroxy-3-[3-[3-(cyanomethoxy)phenyl]-1-oxo-2-propenyl]-2(1H)-quinolinone

Participants

Reaction Steps

In a mixture of 3000 ml of chloroform and 600 ml of dimethylformamide were dissolved 60.00 g of 3-acetyl-4-hydroxy-2(1H)-quinolinone, 142.20 g of 3-(cyanomethoxy)benzaldehyde and 17.64 g of piperidine, and the solution was heated overnight under reflux while water was removed with a Soxhlet extractor filled with molecular sieves. After cooled to room temperature, precipitated crystals were filtered, and washed with 750 ml of tetrahydrofuran and 900 ml of t-butyl methyl ether to obtain 77.59 g of 4-hydroxy-3-[3-[3-(cyanomethoxy)phenyl]-1-oxo-2-propenyl]-2(1H)-quinolinone [Compound No. (10e)] as a yellow crystal.

Provenance & Evidence