Hydrochloric Acid → Methyl 7-methoxy-2-methyl-1H-indole-3-carboxylate

Participants

Reaction Steps

To a 1 L round-bottomed flask equipped with a magnetic stirrer and a N2 bubbler were added 2-methyl-3-trichloroacetyl-7-methoxyindole (22.8 g, 74.37 mmol) and MeOH (150 mL). The mixture was stirred at RT to give a slurry. KOH (42.5 wt %, 2 mL) was added and the reaction stirred for 5 min. HCl (0.1N, 500 mL) was added dropwise. The slurry was stirred at RT for 1 h and filtered. The cake was washed with DI water (3×30 mL) and suction dried for 18 h to give 2-methyl-3-methoxycarbonyl-7-methoxyindole (15.57 g, 96% yield). 1H NMR (CDCl3) δ2.71 (s, 3H), 3.89 (s, 3H), 3.92 (s, 3H), 6.63 (d, J=7.9 Hz, 1H), 7.12 (dd, J=7.9, 8.0 Hz, 1H), 7.66 (d, J=8.0 Hz, 1H), 8.84 (s, 1H).

Provenance & Evidence