Nitrogen → 6-Hydroxyindole

Participants

Reaction Steps

6-Phenylmethoxyindole (3.93 g, 17.6 mmol), was suspended in acetone (350 mL), under N2 and cooled in an ice bath. 10% Palladium on carbon (0.80 g) was added, and the N2 atmosphere was replaced with H2 by alternately placing the reaction flask under vacuum and introducing H2 from a balloon. The cold bath was then removed and the reaction mixture stirred under positive H2 pressure for 16 hours. The reaction mixture was cooled in an ice bath, and N2 reintroduced. The reaction mixture was filtered through a pad of celite and concentrated in vacuo. The crude product was purified by chromatography on silica gel to give 6-hydroxyindole (1.70 g, 73%).

Provenance & Evidence