3-butyryl-8-phthalimido-4(1H)quinolone → 3-Butyryl-4-chloro-8-phthalimidoquinoline

Participants

Reaction Steps

3-Butyryl-8-phthalimido-4(1H)quinolone (36 g, 0.1 mol) was heated under reflux in phosphoryl oxychloride (200 ml) for 1 hour. The solvent was evaporated and the residue dissolved in chloroform and poured into a rapidly stirred mixture of ice, water and ammonia then stirred for 10 minutes. The chloroform layer was washed with brine, dried (anhyd. MgSO4), filtered and evaporated to a brown oil. Chromatography (silica gel/5% methanol in chloroform) gave 3-butyryl-4-chloro-8-phthalimidoquinoline as a light brown oil (21.5g, 57%).

Provenance & Evidence