Acetic Acid → methyl 5-hydroxy-1H-indole-2-carboxylate

Participants

Reaction Steps

5-Hydroxy-1H-indole-2-carboxylic acid (0.50 g, 2.82 mmol) was dissolved in MeOH:CH2Cl2 (1:1, 15 mL), trimethylsilyl diazomethane (2.0 M in hexanes, ˜5.0 mL) was added dropwise until a persistent yellow color formed and the reaction mixture was stirred for 0.5 h. To the solution was added acetic acid (0.5 mL) and the solvent was evaporated. Purification was accomplished by column chromatography (CH2Cl2: MeOH) to afford the title compound (0.55 g, 99%) as a solid. 1H NMR (400 MHz, DMSO-d6): δ ppm 11.59 (br. s., 1H), 8.88 (dd, 1H), 7.23 (d, 1H), 6.85-6.96 (m, 2 H), 6.77 (dd, 1H), 3.81 (d, 3H). MS: m/z 192.2 (M+1).

Provenance & Evidence