N,N,N',N',N'',N''-Hexamethylmethanetriamine → 5-phenoxy-1H-indole

Participants

Reaction Steps

Combine 2-nitro-5-phenoxytoluene (1.15 g, 5.0 mmol) and tris(dimethylamino)methane (0.87 g, 6.0 mmol) in 10 mL dry toluene and heat to reflux under nitrogen. After 2 hours, cool the reaction mixture to room temperature and evaporate the toluene under reduced pressure to form a residue. Dissolve the residue in 15 mL EtOAc, mix with Pd/C (10%, 100 mg), stir at room temperature under 1 atmosphere of hydrogen for 1.5 days. Filter off catalyst and concentrate the filtrate. Chromatograph on silica gel eluting with hexanes/EtOAc give the title compound as a solid: 1H NMR (300 MHz, CDCl3) 6.49–6.50 (m, 1H), 6.93–7.03 (m, 4H), 7.22–7.27 (m, 5H), 8.15 (br, 1H).

Provenance & Evidence