Indole → 5-methoxy-1-methyl-1H-indole

Participants

Reaction Steps

With dimethyl carbonate as a methylating agent, the N-methylation of indole system containing electron-donating groups was also studied. For an example, N-methylation of 5-methoxyindole with dimethyl carbonate at reflux temperature for 5 hours gave 1-methyl-5-methoxyindole in 97% isolated yield. However, other indole substrates, such as gramine, indole-3-methanol, indole3-ethanol and tryptamine gave a complex mixture of unidentified products. These results indicated that N-methylation with dimethyl carbonate is not applicable to such indole systems.

Provenance & Evidence