4-Chloroaniline → (4-Chlorophenyl)hydrazine

Participants

Reaction Steps

To the solution of 1,445 g of p-chloroaniline in 3,375 ml of 38% hydrochloric acid and 5,650 ml of water the solution of 793 g of sodium nitrite in 3.3 L of water is added during 1 hour at -5° to -8° while stirring under nitrogen. After 15 minutes 7,617 g of stannous chloride in 9 L of 38% hydrochloric acid are added during 30 minutes below 25°. The resulting suspension is stirred in an ice bath for one hour, filtered, the residue suspended in 30 L of water, and 5,000 g of solid sodium hydroxide are added during 1 hour at 0°-25°, while stirring under nitrogen. The mixture is extracted twice with 8 L of diethyl ether, the combined extracts washed twice with 4 L of water and once with saturated aqueous sodium chloride, dried, filtered, evaporated and the residue dried at 5 mmHg and room temperature, to yield the p-chlorophenyl-hydrazine melting at 82°-87°.

Provenance & Evidence