Potassium Iodide → HCID 9861832, compound

Participants

Reaction Steps

4-Oxo4,5,6,7-tetrahydroindol-2-carbonitrile (5.5 g) (Estep, K. G.; Synthetic Communications, 1995, 25, 507-514) in DMF (100 mL) was stirred with 3,4-dichlorobenzyl chloride (5.86 g), potassium iodide (cat.) and potassium carbonate (5.5 g) overnight until reaction was complete. The mixture was poured onto ice and partitioned between water and methylene chloride. The organic phase was washed with brine and dried (MgSO4), and the solvents removed in vacuo, to afford a pale yellow solid. Trituration with ether afforded the title compound as a white solid (8.71 g, 91%), NMR d(CDCl3) 2.20 (2H, dt), 2.50 (2H, t), 2.78 (2H, t), 5.20 (2H, s) 6.95 (1H, dd), 7.20 (2H, m), 7.45 (1H, d); M/z (+) 321 (MH+), 319.

Provenance & Evidence