Hydrogen Peroxide → HCID 66604894, compound

Participants

Reaction Conditions

Reaction Steps

Aqueous sodium carbonate (3 M, 700 μL, 2.10 mmol) and aqueous hydrogen peroxide (30%, 700 μL, 6.79 mmol) were added to a suspension of 7-methoxy-3-(4-methoxyphenyl)-9H-carbazole-1-carbonitrile (69 mg, 0.21 mmol) in ethanol (10 mL). The mixture was heated overnight at 60° C. Sodium hydroxide (84 mg, 2.10 mmol) and additional aqueous hydrogen peroxide (30%, 700 μL, 6.79 mmol) were added and heating was continued for a further 17 hr. The ethanol was removed on the rotary evaporator and the white precipitate was collected by filtration, washed with water, and dried under vacuum. Silica gel radial chromatography using step gradient elution with hexane containing 25 to 100% ethyl acetate gave 7-methoxy-3-(4-methoxyphenyl)-9H-carbazole-1-carboxamide (41 mg, 54% yield) as a white solid. MS (ESI) m/z 347.1 (M+H). 1H NMR (DMSO-d6) δ ppm 11.21 (1H, s), 8.45 (1H, d, J=1.22 Hz), 8.29 (1H, br. s.), 8.13 (1H, d, J=1.53 Hz), 8.09 (1H, d, J=8.55 Hz), 7.80 (2H, d, J=8.55 Hz), 7.47 (1H, br. s.), 7.29 (1H, d, J=2.44 Hz), 7.07 (2H, d, J=8.55 Hz), 6.81 (1H, dd, J=8.55, 2.14 Hz), 3.84 (3H, s), 3.83 (3H, s).

Provenance & Evidence