N-[2-(Hydroxymethyl)-1H-indol-5-yl]acetamide → 5-Acetamino-2-indolecarboxaldehyde

Participants

Reaction Steps

To a solution of 15 (100 mg, 0.5 mmol) in ethanol (10 mL) was added MnO2 (250 mg) and the reaction mixture was stirred for 3 h at room temperature. The reaction mixture was filtered and the solid was washed with ethanol. The solvent was removed in vacuo and a grey solid 16 was obtained (97 mg, 100% yield). An analytical sample was recrystallized in ethyl acetate. mp: 200° C. (dec). 1H NMR (DMSO-d6, ppm): 11.80 (s, 1 H, NH), 9.84 (s, 1 H, NH), 9.81 (s, 1 H, CHO), 8.09 (s, 1 H, Ar--H), 7.38-7.32 (m, 3 H, Ar--H), 2.04 (s, 3 H, CH3), Anal. (C11H10N2O2 0.4H2O), C, H, N.

Provenance & Evidence