Indole → 3-(Cyanoacetyl)indole

Participants

Reaction Steps

3-(Cyanoacetyl)indole was prepared by suspending indole (11.71 g, 0.10 mmol) and potassium cyanoacetate (24.6 g, 0.2 mmol) in acetonitrile (300 mL), and to this methanesulphonylchloride (7.7 mL, 0.1 mmol) was added. The resulting mixture was stirred at ambient temperature for 1 h, and then sodium carbonate (10 g in 50 mL water) was added. After 5 min, the organic phase was separated, dried (Na2SO4) and concentrated under reduced pressure. The residue was recrystallised from ethanol (100 mL) to give the desired material as an orange solid (4.31 g), m.p. 226-227°. δH (d6 DMSO) 12.20 (1H, bs), 8.38 (1H, d, J 2.8 Hz), 8.14-8.10 (1H, m), 7.53-7.50 (1H, m), 7.25-7.21 (2H, m) and 4.49 (2H, s).

Provenance & Evidence