Acetanilide → Diphenylamine

Participants

Reaction Steps

The acetanilide II (13.5 g), the particular aromatic bromide III (25 g), potassium carbonate (13.2 g) and copper iodide (1.9 g) were heated (190° C.) and stirred overnight. After cooling to room temperature toluene was added and the precipitate filtered. The solution was concentrated and the excess of bromide removed by distillation under reduced pressure. The residue was dissolved in ethanol (200 ml), potassium hydroxide (10.3 g) was added and the mixture refluxed overnight. Ethanol was evaporated, the residue dissolved in dichloromethane, and washed with brine. The organic layer was dried over MgSO4 and concentrated to obtain the crude diphenyl amine.

Provenance & Evidence