Hydrochloric Acid → HCID 21840843, compound

Participants

Reaction Steps

To 1,2-dichloroethane (150 ml) is added boron chloride (25 g) under ice-cooling, and the mixture is stirred for 15 minutes. To the reaction mixture is added dropwise a solution of 3,4-dimethoxyaniline (36.3 g) in 1,2-dichloroethane (150 ml), and thereto is added 4-cyanopyridine (27.1 g). The reaction mixture is heated under reflux overnight, and thereto is added 2 M hydrochloric acid (160 ml). The mixture is heated with stirring at 80° C. for two hours, and thereto is added a 2 M aqueous sodium hydroxide solution (450 ml) under ice-cooling. The mixture is separated to collect the 1,2-dichloroethane layer, and the aqueous layer is extracted with ethyl acetate. The organic layers are combined, washed, dried and concentrated. The residue is crystallized from ether to give 3,4-dimethoxy-6-isonicotinoylaniline (13.1 g).

Provenance & Evidence