Hydrochloric Acid → methyl 6-hydroxy-1H-indole-2-carboxylate

Participants

Reaction Conditions

Reaction Steps

To a solution of 6-hydroxy-1H-indole-2-carboxylic acid (5.0 g, 28.2 mmol) in MeOH (250 mL) was added concentrated HCl (3 mL) and the reaction mixture was heated (90° C., 3 h). The reaction mixture was cooled (rt) and concentrated in vacuo. The resulting residue was partitioned between EtOAc (50 mL) and H2O (200 mL). The organic layer was separated and the aqueous layer was extracted with EtOAc (2×200 mL). The organic layer was dried, filtered and concentrated in vacuo to provide the title compound as a yellow solid (4.2 g, 77%). MS (ESI): mass calcd. for C10H9NO3, 191.1; m/z found, 192.1 [M+H]+.

Provenance & Evidence