Tryptamine → 1-hydroxyindole

Participants

Reaction Steps

1-hydroxyindole can be prepared in 2 stages from indole by reducing it to triethylsilane in trifluoroacetic acid then by treating the indoline obtained with an aqueous solution of H2O2 (30%) in the presence of a catalytic quantity (20%) of sodium tungstate dihydrate (Na2WO4.H2O) in methanol at 0° C. according to a procedure described in M. Somei, F. Yamada, T. Kurauchi, Y. Nagahama, M. Hasegawa, K. Yamada, S. Teranishi, H. Sato, C. Kaneko Chem. Pharm. Bull. 2001, 49, 87-96. This procedure was used in the preparation, from tryptamine derivatives, of several compounds oxygenated in position 5 of the indole ring such as for example serotonin, the N-methylserotonin and 5-methoxy-N-methyltryptamine.

Provenance & Evidence