Hydrochloric Acid → O-(3-Carboxyphenyl)hydroxylamine

Participants

Reaction Steps

LiOH.H2O (91.0 mg, 2.17 mmol) was added to a solution of O-(3-methoxycarbonyl-phenyl)hydroxylamine 14 (90.4 mg, 0.541 mmol) in a 3/1/1 mL mixture of THF/MeOH/H2O and the reaction was stirred at room temperature. After 24 h the reaction was diluted with H2O (50 mL), acidified to pH-3-4 with 0.5 N HCl, and extracted with EtOAc (3×25 mL). The combined organics were washed with H2O (25 mL) and brine (25 mL), dried over Na2SO4, filtered, and concentrated to afford 3 as a white solid (78.7 mg, 95%). 1H-NMR (500 MHz, d6-DMSO) δ 7.01 (s, 2H), 7.24 (ddd, J=1.4, 2.8, 8.3 Hz, 1H), 7.34 (t, J=7.8 Hz, 1H), 7.46 (dt, J=1.4, 7.3 Hz, 1H), 7.68 (dd, J=1.4, 2.8 Hz, 1H); 13C-NMR (125 MHz, d6-DMSO) δ 113.5, 117.8, 121.3, 129.2, 131.8, 161.7, 167.3; ESI-MS 162 m/z [M-H+]−, C7H6NO3 requires 162.

Provenance & Evidence