p-Toluohydrazide → 4-Methyl-benzoic acid-(1-imino-ethyl)-hydrazide

Participants

Reaction Steps

1.65 g (72 mmol) of sodium are dissolved in 80 mL ethanol. 8.89 g (72 mmol) of ethylacetimidate hydrochloride in 160 mL ethanol are added at ambient temperature and the precipitated sodium chloride is filtered off. The filtrate is combined with 6.00 g (40 mmol) 4-methyl-benzoic acid hydrazide and stirred overnight. The reaction mixture is evaporated down and cooled. The precipitated solid is filtered off and washed with cold ethanol and diethyl ether (5.7 g of white solid). A further 1.2 g of solid are obtained from the filtrate after the removal of the solvent by distillation and recrystallisation from ethanol. Yield: 6.93 g (91%); mass spectroscopy [M+H]+=192.

Provenance & Evidence