Hydroxylamine HCl → HCID 136344373, compound

Participants

Reaction Steps

To a suspension of hydroxylammonium chloride (27.6 mg) in ethanol (1 mL) was added sodium hydrogen carbonate (33.4 mg), and this mixture was heated under reflux for 45 minutes. Then, a solution of 6-(6-methyl-2-phenyl-1H-indol-3-ylmethyl)pyridine-2-carbonitrile (61 mg) in ethanol (1.3 mL) was added dropwise thereto under ice-cooling, and the mixture was heated under reflux for additional 3.5 hours. The reaction mixture was left to be cooled and concentrated under reduced pressure. To the residue was added water, followed by extraction with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluting solvent: ethyl acetate-hexane) to obtain the title compound (60.8 mg). 1H-NMR (CDCl3) δ ppm: 2.47 (3H, s), 4.42 (2H, s), 5.64 (2H, br s), 6.48-6.84 (1H, br), 6.90-6.97 (1H, m), 7.08-7.14 (1H, m), 7.18-7.23 (1H, m), 7.32-7.49 (4H, m), 7.52 (1H, t, J=7.8 Hz), 7.54-7.61 (2H, m), 7.66-7.74 (1H, m), 8.06 (1H, br s). ESI-MS (m/z): 357 (M+H)+

Provenance & Evidence