5-Methoxy-2-nitro-4-(trifluoromethyl)benzene acetonitrile → 5-Methoxy-6-(trifluoromethyl)-1H-indole

Participants

Reaction Steps

(5-Methoxy-2-nitro-4-trifluoromethylphenyl)acetonitrile (D9) (85 g, 0.327 mol) in ethanol/water (9:1, 1.6 l) and glacial acetic acid (16 ml) was hydrogenated over 10% palladium on carbon (50 g) at 50 psi for 0.5 h at room temperature. The reaction mixture was filtered and evaporated in vacuo. The residue was partitioned between aqueous K2CO3 (1 l) and dichloromethane (2×1 l) and the combined organic extract was dried Na2SO4) and evaporated to afford the title indole (67.63 g, 96%) as a grey solid.

Provenance & Evidence