Ethanol → HCID 178488793, compound

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Reaction Steps

A mixture of 4-(3-bromo-4-methoxyphenyl)-3-methyl-3-nitro-4,5-dihydro-3H-pyrazole (100 mg, 0.32 mmol) and 0.5 mL of water was stirred at room temperature and 2.0 mL of 40% aqueous potassium hydroxide was added. After the mixture had been sonicated for 5 min, 1.0 mL of 95% ethanol was added, followed 20 min later by another 0.5 mL of 95% ethanol. After 15 min, the solution was extracted with 2×20 mL of ether. The ether extracts were washed in succession with 10 mL of saturated aqueous sodium chloride solution, dried (sodium sulfate), decanted, and evaporated to give a white solid. Flash column chromatography on 4 g of silica gel eluting with 15-20% ethyl acetate in dichloromethane gave 80 mg of white solid (94% yield). 1H NMR (400 MHz, CDCl3): δ 7.62 (s, 1H), 7.30 (dd, 1H, J=8, 2 Hz), 6.94 (d, 1H, J=8 Hz), 3.93 (s, 3H), 2,43 (s, 3H). Mass spectrum (NH3CI): m/e=267 (M+1).

Provenance & Evidence