O-Toluidine → 3-Benzoyl-4-(2-methylphenylamino)-8-methoxyquinoline

Participants

Reaction Steps

3-Benzoyl-4-chloro-8-methoxyquinoline (3.0 g, 0.01 mol) was heated under reflux in 1,4-dioxan (100 ml) with o-toluidine (5.0 ml) for 1 hour. The solvent was evaporated and the residue was dissovled in dichloromethane, and washed with dilute hydrochloric acid, sodium hydrogen carbonate solution, water and brine. The organic solution was dried and evaporated to an oil which was chromatographed (silica gel, 1% methanolic ammonia in dichloromethane). 3-Benzoyl-4-(2-methylphenylamino)-8-methoxyquinoline was isolated as crystals (0.95 g, 25.8%) from ether/hexane, m.p. 128-130.

Provenance & Evidence