Ethanol → HCID 178513283, compound

Participants

Reaction Conditions

Reaction Steps

Hydroxylamine hydrochloride (56 mg, 0.804 mmol) was added to a solution of NaHCO3 (68 mg, 0.804 mmol) in water (0.5 mL). Ethanol (1.5 mL) was added followed by 2-(1H-imidazol-4-yl)benzonitrile in THF (0.5 mL) and the reaction mixture was heated at 80° C. for 18 h. Solvents were removed under reduced pressure and the remaining solution poured into water and extracted with EtOAc (2×20 mL). The combined organic layers were washed with brine (10 mL), dried, and concentrated. The residue was purified by flash column chromatography (silica gel, 5%-30% MeOH/DCM) to afford the desired product as a white solid (20 mg, 0.099 mmol, 25%). 1H NMR (DMSO-d6): 3.13 (s, 1H), 5.75 (s, 1H), 7.16-7.38 (m, 3H), 7.65 (s, 1H), 7.79 (s, 1H), 7.92 (d, 1H, J=7.6 Hz), 9.27 (s, 1H)

Provenance & Evidence