Dimethylformamide → 6-phenoxy-1H-indole

Participants

Reaction Steps

Combine 4-phenoxy-1-methyl-2-nitro-benzene (6 g, 26.2 mmol) and DMF dimethylacetal (15.6 g, 131 mmol) in 60 mL dry DMF and heat at 170° C. for 16 hours. Cool to room temperature and concentrate to dryness. Dissolve residue in 50 mL EtOAc and hydrogenate with 2 g 5% Pd/C and hydrogen for 3 hours at atmospheric pressure. Filter through celite and concentragte to an oil. Purify by chromatography using Hex/EtoAC to obtain a tan solid: ISMS 210 (M+1) 1H NMR (CDCl3) 8.08 (bs, 1H), 7.61–7.59 (m, 1H), 7.34–7.29 (m, 2H), 7.18–7.17 (m, 1H), 7.18–7.0 (m, 4H), 6.92–6.89 (m, 1H), 6.56–6.54 (m, 1H).

Provenance & Evidence