Hydroxylamine → HCID 42606653, compound

Participants

Reaction Steps

To a stirring solution of methyl 5-methoxy-2-(thiophen-2-yl)benzoate 10 (0.13 g, 0.524 mmol) and a solution of 50% hydroxylamine in water (0.53 mL, 0.524 mmol) in THF (1 mL) and MeOH (1 mL) was added KOH (0.117 g, 2.094 mmol) and the reaction mixture was allowed to stir at room temperature for 3 hours. The reaction mixture was solvent evaporated, diluted with DCM, washed with 5% KHSO4, brine, dried over MgSO4, filtered and solvent evaporated to provide title compound 11 (50 mg, 38% yield) as a white solid after trituration (overnight, DCM). 1H NMR (400 MHz, DMSO-d6) δ (ppm): 10.87 (s, 1H), 9.06 (s, 1H), 7.49 (d, J=1.2 Hz, 1H), 7.45 (dd, J=15.5, 1.2 Hz, 1H), 7.14 (dd, J=3.5, 1.2 Hz, 1H), 7.05 to 7.02 (m, 2H), 6.84 (d, J=2.7 Hz, 1H), 3.78 (s, 3H). LRMS (ESI): (calc.) 249.05 (found) 250.1 (MH)+

Provenance & Evidence