Potassium Hydroxide → HCID 72330477, compound

Participants

Reaction Steps

Hydroxylamine hydrochloride (0.55 g, 8 mmol) in methanol (3 mL) was mixed with KOH (0.45 g, 8 mmol) in methanol (3 mL) at 0° C., and sonicated for 2 minutes and the white precipitate formed was filtered. The filtrate was added to the methyl 6-(4-(3-(cyclopropylamino)-2-(4-fluorophenyl)-3-oxoprop-1-enyl)benzamido)hexanoate (0.2 g, 0.4 mmol) in DCM (1.5 mL) and the mixture was stirred at room temperature, for 30 minutes. The reaction mixture was diluted with water (200 mL) and extracted with ethyl acetate (3×100 mL). The ethyl acetate layer was washed with water (100 mL), dried over anhydrous Na2SO4 and concentrated to afford the title compound (0.040 g, 20% yield). 1H NMR (DMSO-d6) δ (ppm): 0.52 (2H, m, 0.63-0.64 (2H, m, —CH2), 1.23-1.25 (2H, m, CH2), 1.44-1.50 (4H, m, CH2), 1.90-1.94 (2H, m, CH2), 2.74-2.75 (1H, m, —CH), 3.17-3.19 (2H, m, CH2), 7.04 (2H, d, Ar—H), 7.16-7.22 (4H, m, Ar—H), 7.28 (1H, s, ═C), 7.63 (2H, d, Ar—H), 7.89 (1H, d, NH), 8.36 (1H, t, NH), 8.66 (1H, s, —OH), 10.32 (1H, s, NH), MS m/z: 452.2 (M+−1).

Provenance & Evidence