Water → 5-Nitroindole-2-carboxylic acid

Participants

Reaction Steps

5-Nitro-1H-indole-2-carboxylic acid ethyl ester 15 (194 mg, 0.83 mmol) and KOH (342 mg, 5.25 mmol) were stirred in MeOH/water (8 mL/4 mL) at room temperature for 21.5 h. More water was added to dilute the solution. The mixture was concentrated to remove the organic solvent. The remaining solution was washed with DCM (100 mL). The aqueous solution was adjusted with 1 N HCl to pH 2.9, extracted with EtOAc (2×15 mL). The combined EtOAc extraction was washed with brine, dried over sodium sulfate, concentrated to afford the product as solid (185.5 mg, 97% yield). 1H-NMR (DMSO-d6): 8.718 (d, J=2.0-2.5 Hz, 1 H, Ar—H), 8.116 (dd, J=2.0-2.5 Hz and 9.0-9.5 Hz, 1 H, Ar—H), 7.583 (d, J=9.0-9.5 Hz, 1 H, Ar—H), 7.378 (d, J=1.5 Hz, 1 H, Ar—H). LC-MS: 207.1 (MH+).

Provenance & Evidence