Propynonitrile (1.54 g, 30.2 mmol) was mixed with hydroxylamine hydrochloride (2.10 g, 30.2 mmol), 10% aqueous sodium hydroxide (12.1 mL, 30.2 mmol) and methanol (12 mL) and the reaction was stirred for 12 hours at 30 °C. After completion of the reaction, the reaction mixture was extracted with ethyl acetate. The organic phases were combined, dried with anhydrous magnesium sulfate and concentrated under reduced pressure to remove the solvent. The resulting crude product was purified by silica gel column chromatography (eluent: ethyl acetate) to afford the target compound 5-aminoisoxazole (760 mg, 29.9% yield) as solid.1H-NMR (CDCl3) δ: 4.51 (2H, br s), 5.11 (2H, d, J = 2.1 Hz), 7.96 (2H, d, J = 2.1 Hz).
