p-Toluenesulfonic acid → 8-chloro-3-(4-chlorobenzyl)-5-hydroxy-2-methyl-1H-quinolin-4-one

Participants

Reaction Conditions

Reaction Steps

A mixture of 3-amino-4-chlorophenol (2.5 g), 2-(4-chlorobenzyl)-3-oxobutyric acid ethyl ester (4.7 g) and toluene-4-sulfonic acid (0.3 g) was heated at 160° C. under nitrogen for 10 hours. The mixture was cooled to room temperature and the residue triturated with methanol and then crystallised from butan-1-ol to afford a beige powder. Purification by column chromatography on silica gel, eluting with a mixture of ethyl acetate and dichloromethane (0:1 to 1:0 by volume) gave title compound as a yellow solid, 0.77 g.

Provenance & Evidence