Hydrazine, dihydrochloride → HCID 178496120, compound

Participants

Reaction Steps

To a solution of 2-(2-(methyloxy)-3-{[2-(methyloxy)ethyl]oxy}phenyl)-3-oxobutanenitrile (0.17 g, 0.65 mmol) in ethanol (5 mL) was added hydrazine dihydrochloride (99 mg, 0.94 mmol). The resulting mixture was heated at reflux for 1 hour. It was cooled, poured into a saturated sodium bicarbonate solution (10 mL), and the mixture was extracted with ethyl acetate (3×10 mL). The combined extract was washed with aqueous sodium bicarbonate solution, brine, dried over sodium sulfate, filtered and concentrated to give an oily residue which was purified by flash chromatography (silica gel, 5% methanol in dichloromethane) to provide 3-methyl-4-(2-(methyloxy)-3-{[2-(methyloxy)ethyl]oxy}phenyl)-1H-pyrazol-5-amine (115 mg, 0.42 mmol, 65% yield). MS (EI) for C14H19N3O3: 278 (MH+).

Provenance & Evidence