Ethanol → 4-Cyclohexylphenylhydrazine hydrochloride

Participants

Reaction Conditions

Reaction Steps

To a slurry a 4-cyclohexylaniline (350.6 g) and ethanol (330 ml) in 30% HCl (1470 ml) was added a solution of sodium nitrite (151.8 g) in water (735 ml), while maintaining the temperature between -8 to -2° C. The reaction was stirred for an additional four hours at -2 to 10° C. A solution of tin (II) chloride dihydrate (1353.8 g) in 30% HCl (1470 ml) was added slowly, and the resulting white suspension was cooled overnight. The crude product was collected by vacuum filtration and washed with 1 N hydrochloric acid, and ether. Recrystallization in 6 L of methanol gave 300 g of the desired product as fine long needles, m.p. 251-254° C.

Provenance & Evidence