4-Toluenesulfonyl chloride → HCID 67377141, compound

Participants

Reaction Steps

To a solution of 1-oxo-2,3,4,9-tetrahydro-1H-carbazole-6-carbonitrile (intermediate 2a) (0.20 g, 0.95 mmol) in THF (2.0 mL), KOH (0.27 g, 4.8 mmol) in water was added followed by TsCl (0.27 g, 1.4 mmol). The reaction mixture was stirred at room temperature for 12 h and then extracted with EtOAc (3×15 mL). The combined organic extracts were dried over Na2SO4 and concentrated in vacuo to give the crude compound which was purified by column chromatography [EtOAc-hexane (1:4) as eluant] to obtain the title compound as an off-white solid (0.23 g, 65%). 1H NMR (200 MHz, CDCl3, δ in ppm) 8.0 (d, J=8.4 Hz, 2H), 7.82 (d, J=2.0 Hz, 1H), 7.43 (dd, J=12.0, 2.0 Hz, 1H), 7.39 (d, J=8.4 Hz, 2H), 7.30 (d, J=12.5 Hz, 1H), 2.95 (t, J=9.0 Hz, 2H), 2.66 (t, J=9.0 Hz, 2H), 2.40 (s, 3H), 2.30 (m, 2H).

Provenance & Evidence