Sodium Hydroxide → HCID 22497217, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 2,2,2-trifluoro-1-(1-isopropyl-6-nitro-1H-indol-3-yl)-ethanone (525 mg, 1.75 mmol) in a 20% aqueous sodium hydroxide solution (10 mL) was heated at 1110° C. for 2 h. At this time, the reaction was cooled to 25° C., partitioned between water (75 mL) and ethyl acetate (75 mL), and treated with a 1N aqueous hydrochloric acid solution (25 mL). The organic layer was washed with water (1×50 mL) and a saturated aqueous sodium chloride solution (1×50 mL), dried over magnesium sulfate, filtered, and concentrated in vacuo to afford 1-isopropyl-6-nitro-1H-indole-3-carboxylic acid (436 mg, 99%) as a yellow solid: mp 242-243° C.; EI-HRMS m/e calcd for C12H12N2O4 (M+) 248.0797, found 248.0796.

Provenance & Evidence