Ammonium Chloride → HCID 136166859, compound

Participants

Reaction Steps

A solution of 3-(4-dimethylamino-phenyl)-3-phenyl-1-pyridin-4-yl-propan-1-one (838 mg), hydroxylamine hydrochloride (353 mg) and sodium hydrogencarbonate (426 mg) in ethanol/water (21 mL, 20:1) was heated under reflux for 2 hours. A saturated aqueous solution of NH4Cl was added to the reaction mixture and extraction was made with EtOAc (2×). The organic layers were combined, washed with brine, dried over Na2SO4, filtered and concentrated in vacuo. Column chromatography on silica gel (EtOAc/n-heptane 2:1) gave (E)-3-(4-dimethylamino-phenyl)-3-phenyl-1-pyridin-4-yl-propan-1-one oxime (420 mg, 48%) as a white foam, MS (ESI+): m/z=346.1 ([M+H]+), (Z)-3-(4-dimethylamino-phenyl)-3-phenyl-1-pyridin-4-yl-propan-1-one oxime (20 mg, 2%) as a colorless oil, MS (ESI+): m/z=346.1 ([M+H]+) and 3-(4-dimethylamino-phenyl)-3-phenyl-1-pyridin-4-yl-propan-1-one oxime as a mixture of isomers (313 mg, 36%), MS (ESI+): m/z=346.1 ([M+H]+).

Provenance & Evidence