Sulfuric Acid → 7,8-Dichloro-2,3,4,9-tetrahydro-1H-carbazol-1-one

Participants

Reaction Conditions

Reaction Steps

To a solution of 2-(2-(2,3-dichlorophenyl)hydrazono)cyclohexanone (1.6 g, 5.9 mmol) in MeCN (10 mL), H2SO4 (0.6 mL, 0.01 mmol, 1.6M solution) was added and the reaction mixture was stirred at 80° C. for 16 h, cooled to room temperature, basified with NaHCO3 and extracted with EtOAc (2×20 mL). The combined organic extracts were dried over Na2SO4 and concentrated in vacuo to give the crude compound which was purified by silica gel chromatography [EtOAc-hexane (1:4) as eluant] to provide the title compound as a solid (0.90 g, 60%). 1H NMR (200 MHz, DMSO-d6, δ in ppm) 12.13 (bs, 1H), 7.72 (d, J=8.8 Hz, 1H), 7.31 (d, J=8.8 Hz, 1H), 2.99 (t, J=8.4 Hz, 2H), 2.62-2.2.56 (m, 2H), 2.21-2.12 (m, 2H).

Provenance & Evidence