3-Cyclohexylcarbonyl-4-chloro-8-methoxyquinoline → 3-Cyclohexylcarbonyl-4-(2-methylphenylamino)-8-methoxyquinoline

Participants

Reaction Steps

3-cyclohexylcarbonyl-4-chloro-8-methoxyquinoline (5.0 g, 0.017 mol) was heated under reflux in a mixture of 1,4-dioxan (50 ml) and o-toluidine (2.0 ml) for 2 hours. The reaction mixture was evaporated and the residue dissolved in dichloromethane, washed with sodium hydrogen carbonate solution and brine. The organic solution was dried, evaporated and chromatographed (silica gel, dichloromethane) to affort an oil, which on trituration with hexane-ether gave 3-cyclohexylcarbonyl-4-(2-methylphenylamino)-8-methoxyquinoline as yellow crystals (0.58 g, 9.4%) m.p. 115°-7° C.

Provenance & Evidence