Methyl iodide → 1h-Indole-3-acetonitrile, 6-nitro-

Participants

Reaction Steps

To a stirred solution of 44.27 g (0.204 mol) of 6-nitrogramine (12) [Jackson B. Hester J. Org. Chem., 29: 1158 (1964)] in 450 ml of acetonitrile 44.59 g (0.31 mol) of methyl iodide was added at 0-5° C. over a period of an hour. The reaction mixture was stirred at room temperature for three hours, then a solution of 26.6 g (0.543 mol) of sodium cyanide in 225 ml of water added at once. The reaction mixture was heated at 32° C. overnight, cooled to room temperature and the product extracted 3 times with a total of 800 ml of ethyl acetate and 300 ml of water. The combined extracts were washed with water, 1N-HCl solution, a saturated sodium bicarbonate solution, dried on MgSO4 and the solvent evaporated in vacuo. The orange-brown residue (41.3 g) was dissolved in 200 ml of warm ethyl acetate and passed through a small pad of silica gel to produce 28.9 g (70.4%) of (6-nitro-1H-indolyl-3-yl)-acetonitrile (13) as a yellow solid after evaporation of the solvent.

Provenance & Evidence