Triethylamine → N'-t-butyl-N-benzoyl-N'-nicotinoylhydrazine

Participants

Reaction Conditions

Reaction Steps

A solution of N'-t-butyl-N-benzoylhydrazine (2.0 g) and nicotinoyl chloride hydrochloride in 20 ml of methylene chloride at 23° C. was treated dropwise with triethylamine (4 ml). The reaction mixture was stirred at 23° C. for 0.5 hours. Solids were removed by filtration. The filtrate was diluted with N/10 HCl and ether. The layers were separated and the organic layer was washed with N/10 HCl. The aqueous layer was neutralized with solid sodium bicarbonate and extracted with ether. The ether extracts were treated with charcoal and then dried with magnesium sulfate. Evaporation of solvents afforded a yellow oil which was chromatographed on silica gel using 10% CH3OH, 40% CH2Cl2, 50% Et2O as eluant to afford N'-t-butyl-N-benzoyl-N'-nicotinoylhydrazine as a yellow foam. m.p. 60°-63° C.

Provenance & Evidence