Phosphorus oxychloride → 4-Chloro-3-(2-chloroethyl)-8-methylcinnoline

Participants

Reaction Steps

3-(2-Chloroethyl)-8-methyl-4-oxo-(1H)-cinnoline (9 g, 0.04 mol) and phosphorus oxychloride (100 ml) were heated under reflux for 2 hours. The excess phosphorus oxychloride was evaporated under reduced pressure and the residue was poured onto ice, basified with concentrated ammonia solution and extracted with chloroform (3×200 ml). The chloroform extracts were combined, dried over magnesium sulphate, filtered and evaporated under reduced pressure to give a dark brown solid. Recrystallization from diethyl ether/petroleum ether (b.p. 40-60°) gave an analytically pure sample, m.p. 102-104°

Provenance & Evidence