Phenylhydrazine → N'-phenyl-2-pyridin-4-ylacetohydrazide

Participants

Reaction Steps

N-[3-(dimethylamino)propyl]-N′-ethylcarbodiimide hydrochloride (2.06 g, 10.76 mmol, 2.02 mmol), 1H-1,2,3-benzotriazol-1-ol hydrate (1.45 g, 10.76 mmol), N,N-diisopropylethylamine (4.69 mL, 26.9 mmol), and phenyl hydrazine (970 mg, 8.97 mmol) were added to a solution of 4-pyridylacetic acid hydrochloride (1.23 g, 8.97 mmol) in dimethylformamide (10 mL). After 16 h, the reaction was worked up with dichloromethane and saturated sodium bicarbonate. The organic extracts were washed with brine, dried over sodium sulfate, filtered and concentrated. Purification by silica gel chromatography (99% dichloromethane→12% methanol {1% ammonium hydroxide}/dichloromethane) gave the title compound (400 mg). MS 228.5 (M+1)

Provenance & Evidence