Sodium Hydroxide → 5-acetamido-1H-indole-2-carboxylic Acid

Participants

Reaction Steps

3N NaOH (2 mL) was added to a solution of 3 (250 mg, 1.02 mmol) in methanol (7 mL) and the reaction mixture was stirred overnight at room temperature. The reaction mixture was evaporated and water (5 mL) was added. The solution was neutralized to pH 2 using 20% HCl and the precipitate was filtered and washed with water. 4 was obtained as a grey powder (158 mg, 71% yield), mp: 260° C. (dec). 1H NMR (DMSO-d6, ppm): 11.62 (s, 1 H, NH), 9.77 (s, 1 H, NH), 7.98-7.97 (d, 1 H, J=1.4 Hz, Ar--H), 7.36-7.28 (m, 2 H, Ar--H), 7.02 (d, 1 H, J=1.5 Hz, Ar--H), 2.03 (s, 3 H, CH3CO), Anal. (C11H10N2O3 0.6H2O), C, H, N.

Provenance & Evidence