1H-Indole-5-Carboxylic Acid → methyl 1H-indole-5-carboxylate

Participants

Reaction Steps

Combine 5-carboxyindole (7.2 g, 44.7 mmol) in 400 mL dichloromethane and 100 mL MeOH and treat dropwise with 35 mL 2 M TMS diazomethane in hexanes. Stir overnight at ambient temperature. Concentration under vacuum to give the title compound as a solid: Analysis for C10H9NO2 0.1H2O: calcd: C, 67.86; H, 5.24; N, 7.91; found: C, 68.03; H, 5.15; N, 7.98; 1H NMR (CDCl3) 8.44 (bs, 1H), 8.412–8.409 (m, 1H), 7.91–7.88 (m, 1H), 7.46–7.38 (m, 1H), 7.26–7.24 (m, 1H), 6.64–6.63 (m, 1H), 3.92 (s, 3H); ISMS 176 (M+1).

Provenance & Evidence