(5-nitro-1H-indol-2-yl)methanol → 5-Nitro-1H-indole-2-carbaldehyde

Participants

Reaction Steps

A solution of crude (5-nitro-1H-indol-2-yl)methanol (3.60 g, 18.7 mmol) in chloroform (200 mL) was heated at 50° C. with manganese dioxide (20 g, 0.23 mol) for 3 h. The reaction mixture was then filtered through Celite and concentrated to give 5-nitro-1H-indole-2-carbaldehyde (904) (2.04 g, 57% through two steps). 1H NMR δ [(CD3)2SO] 12.64 (br, 1H), 9.96 (s, 1H), 8.83 (d, J=2.3 HZ, 1H), 8.18 (dd, J=9.0 Hz, 2.3 Hz, 1H), 7.69 (d, J=0.7 Hz, 1H), 7.62 (d, J=9.0 Hz, 1H).

Provenance & Evidence