(2-Nitro-5-trifluoromethylphenyl) acetonitrile → 5-(trifluoromethyl)-1H-indole

Participants

Reaction Steps

(2-Nitro-5-trifluoromethylphenyl)acetonitrile (D4, 1.9 g, 0.0088 mole) in 90% EtOH/H2O (25 ml) and glacial acetic acid (0.25 ml) was hydrogenated at 50 psi in the presence of 10% Pd/C (1 g) at room temperature for 2 hours. After filtration of the catalyst through kieselguhr, the solvent was removed in vacuo. The residue was basified with saturated aqueous potassium carbonate solution, extracted into DCM, dried (Na2SO4) and evaporated in vacuo. The residue was chromatographed on silica gel eluting with 30% ethyl acetate/60-80° petroleum ether to afford the title compound (1.0 g, 65%) as an off white solid.

Provenance & Evidence