N-Methyl-5-benzyloxyindole → 1-Methyl-1H-indol-5-ol

Participants

Reaction Conditions

Reaction Steps

5-(Benzyloxy)-1-methyl-1H-indole (Example 46, 254 mg, 1.07 mmol) was dissolved in EtOH (15 mL) and 20% palladium (II) hydroxide on carbon (30.0 mg) was added. Ammonium formate (540 mg, 8.6 mmol) was added, and the mixture was stirred for 30 min at rt and subsequently for 2 h at 35° C. The catalyst was removed by filtration, and the filtrate was concentrated under reduced pressure. The residue was taken up in water, and the aqueous solution was extracted with EtOAc (2×). The combined organic phases were dried over Na2SO4, filtered, and concentrated under reduced pressure to provide 141 mg (90%) of the title compound as a white crystalline solid. 1H NMR (400 MHz, CDCl3): δ 3.78 (s, 3H), 6.33 (br, 1H), 6.79 (d, 1H), 7.03 (br, 2H), 7.19 (d, 1H).

Provenance & Evidence