Aniline → Formanilide

Participants

Reaction Conditions

Reaction Steps

Into a 1-liter Parr autoclave equipped with an agitator, thermowell, rupture disc and cooling coils are placed 84 g. (0.9 mole) of aniline, 16 g. (0.1 mole) of potassium formanilide and 150 g. of methanol. The autoclave is closed and purged with CO. The temperature is raised to 100° C. with atm. steam and CO is introduced at 28 kg/cm2 pressure. Absorption is rapid and little or no heat of reaction is noted. The reaction is run for 31/2 hours, the autoclave cooled to 15° C. and the excess CO vented. The methanol is removed by distillation, xylene added and resulting xylene solution washed with 10 ml. of conc. hydrochloric acid and 200 ml. of water. The organic layer is separated and analyzed by gas-liquid chromatography. The yield of formanilide expected is approximately 93%.

Provenance & Evidence