Methyl iodide → 2-(5-nitro-1H-indol-3-yl)acetonitrile

Participants

Reaction Steps

Dissolve the N,N-dimethyl-5-nitrotryptamine obtained above in 200 mL dry DMSO, treat with iodomethane (7.7 mL, 17.5 g, 124 mmol), and stir for 1 hour at ambient temperature. Add KCN (40 g, 621 mmol) and 18-crown-6 (0.5 g). Warm the reaction to 110° C. for 45 minutes, cool, poured onto ice then saturate with NaCl. Extract the quenched reaction mixture with EtOAc, combine the extracts, and wash 3 times with brine. Dry over MgSO4 and concentrate under vacuum chromatograph on silica gel eluting with 1% MeOH in CHCl3 to give (5-nitro-1H-indol-3-yl)acetonitrile as a solid: FDMS 201 (M+); Analysis for C10H7N3O2: calcd: C, 59.70; H, 3.51; N, 20.89. found: C, 59.32; H, 3.52; N, 20.56.

Provenance & Evidence