Hydrochloric Acid → 3-(2-Chloroethyl)-8-methyl-4(1H)-cinnolinone

Participants

Reaction Steps

To a solution of 1-(2-amino-3-methylphenyl)-4-chlorobutan-1-one hydrochloride (20 g, 0.081 Mol) and concentrated hydrochloric acid (1000 ml) at 0° was added dropwise a solution of sodium nitrite (6.07 g, 0.088 mol) in water (50 ml) maintaining the temperature below 5°. The reaction mixture was stirred at room temperature for 20 hours. The solvent was evaporated under reduced pressure to give a solid. The solid was washed with sodium acetate solution and collected by filtration and dried, 13.5 g. Recrystallization from methanol gave the title compound, m.p. 222-225°

Provenance & Evidence