Ammonium Chloride → HCID 136167025, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 3-(4-bromo-phenyl)-1-(2-methyl-pyridin-4-yl)-3-(2-trifluoromethyl-phenyl)-propan-1-one (80 mg), hydroxylamine hydrochloride (37 mg) and sodium hydrogencarbonate (45 mg) in a mixture of ethanol (4 mL) and water (0.7 mL) was heated under reflux for 2 hours. A saturated solution of NH4Cl was added, the phases were separated and the inorganic one was extracted with EtOAc (2×). The combined organic layers were washed with brine, dried over Na2SO4, filtered and concentrated in vacuo. The crude product was dissolved in DME (5 mL) and HCl in dioxane (4M, 0.45 mL) were added at rt. The reaction mixture was stirred at 50° C. overnight, was concentrated and dissolved in ethyl acetate (5 mL) and a saturated aqueous solution of NaHCO3 (0.1 mL). A saturated aqueous solution of NH4Cl was added, the phases were separated and the inorganic one was extracted with EtOAc (2×). The combined organic phases were washed with brine, dried over Na2SO4, filtered and concentrated in vacuo. The crude product was purified by flash chromatography on silica gel (CH2Cl2/MeOH 95:5) to yield the title compound (65 mg, 79%) as a white foam, MS (ESI+): m/z=463.1 ([M+H]+, 1Br).

Provenance & Evidence