Ammonium Chloride → (1-tosyl-1H-indol-6-yl)methanamine

Participants

Reaction Steps

4-Aminomethylindole, 5-aminomethylindole and 6-aminomethylindole are known compounds. It is sometimes convenient to protect the indole nitrogen and in those instances a tosyl group was first introduced. 1-Tosyl-1H-indole-6-carbonitrile (CASRN31274-87-1) was reduced with H2 and RaNi in 7N ammonical methanol to afford the corresponding aminomethyl derivative. 1-Tosyl-1H-indole-4-carbaldehyde was converted to the oxime and reduced with Zn and NH4Cl in EtOH to afford (1-tosyl-1H-indol-6-yl)methanamine.

Provenance & Evidence