Sodium Hydroxide → N-(3,4-Dichlorobenzyl)-5-hydroxyindole-2-carboxylic acid

Participants

Reaction Steps

Sodium hydroxide (2M, 3 ml) was added to a stirred solution of ethyl N-(3,4-dichlorobenzyl)-5-hydroxyindole-2-carboxylate (0.1 g) in THF (3 ml) and methanol (1.5 ml). The reaction was stirred at ambient temperature for 4 hours. The reaction was concentrated in vacuo and the residue was dissolved in water (5 ml). The solution was acidified by the addition of aqueous hydrochloric acid (2M, 4 ml) precipitating the product as a white solid. The product was filtered, washed with water and dried in vacuo to yield the title compound (82 mg, 89%). NMR: δ 5.77 (s, 2H), 6.81 (dd, 1H), 6.89 (dd, 1H), 6.95 (d, 1H), 7.13 (s, 1H), 7.26 (d, 1H), 7.34 (d, 1H), 7.52 (d, 1H), 9.01 (s, 1H), 12.85 (s, 1H); m/z 334 (M−H+).

Provenance & Evidence