Potassium Hydroxide → HCID 86645066, compound

Participants

Reaction Steps

Hydroxylamine hydrochloride (1.2 g, 17.5 mmol) in methanol (7.5 mL) was mixed with KOH (1.2 g, 17.5 mmol) in methanol (4 mL) at 0° C. and the reaction mixture was sonicated for 5 minutes. A white precipitate was formed which was filtered. The filtrate was immediately added to the ethyl-3-(4-((2,3-diphenylacrylamido)methyl)phenyl)acrylate (0.4 g, 0.9 mmol) followed by the addition of KOH. (0.14 g, 2.4 mmol) and the mixture was stirred at room temperature for 1 hour. Reaction mixture was diluted with water 20 mL and extracted with ethyl acetate, (100 mL). The organic layer was washed successively with water (3×50 mL) and brine solution (3×50 mL). The organic layer was dried over Na2SO4 and concentrated to give the crude compound, triturated with dichloromethane (20 mL), to afford the title compound as a pure colorless solid (0.040 g, 10% yield). 1H NMR (DMSO-d6) δ (ppm): 4.02-4.04 (2H, d, —CH2), 6.41-6.45 (1H, d, ═CH), 7.01-7.03 (2H, d, Ar—H), 7.17-7.22 (5H, m, Ar—H), 7.28-7.30 (2H, d, Ar—H), 7.41-7.46 (4H, m, Ar—H & ═CH), 7.46 (1H, s, ═CH), 7.50-7.52 (2H, d, Ar—H), 7.99-8.01 (1H, t, —NH), 9.03 (1H, s, —OH), 10.74 (1H, s, —NH). MS m/z: 399.1 (M++1). The following compounds were prepared according to the above procedure

Provenance & Evidence