Hydrochloric Acid → 3-(4-Nitrophenyl)isoxazole-5-carboxylic acid

Participants

Reaction Steps

Ethyl 3-(4-nitrophenyl)isoxazole-5-carboxylate (11 g) was dissolved in THF (220 ml). 1 Molar aqueous NaOH (210 ml) was added and stirred at RT for 15-20 minutes. The reaction mass was acidified with 1 molar HCl. The reaction mixture was extracted with ethyl acetate, organic layer washed with brine, dried over Na2SO4 and concentrated under reduced pressure to get off white solid. Solid was crystallized from acetone/Pet ether to yield 8 g (81%) white solid. MS (ES+): m/z 235 (M+1); 1H NMR (DMSO-d6, 300 MHz) δ: 8.39 (d, 2H), 8.27 (d, 2H), 7.97 (s, 1H).

Provenance & Evidence