Ammonium Chloride → HCID 52947474, compound

Participants

Reaction Conditions

Reaction Steps

1-Oxo-2,3,4,9-tetrahydro-1H-carbazole-6-carbonitrile (0.12 g, 0.57 mmol) was dissolved in anhydrous THF (5 mL), cooled to 0° C., and methyl magnesium chloride (0.12 g, 1.71 mmol, 3M in THF) was added dropwise. The reaction mixture was warmed to room temperature and stirred for 3 h at room temperature then cooled to 0° C., saturated NH4Cl (10 mL) was added and then extracted with EtOAc (4×25 mL). The combined organic extracts were dried over Na2SO4 concentrated under reduced pressure to give the crude material which was purified by column chromatography [EtOAc-hexane (3:7) as eluant] to obtain the title compound (0.03 g, 23%). 1H NMR (500 MHz, DMSO-d6, δ in ppm) 11.4 (s, 1H), 7.9 (s, 1H), 7.42 (d, J=12.0 Hz, 1H), 7.39 (d, J=12.0 Hz, 1H), 5.0 (s, 1H), 2.64-2.61 (m, 2H), 2.0-1.7 (m, 4H), 1.4 (s, 3H). IR cm−1 2216 (CN).

Provenance & Evidence