Indole → 5-methoxy-1-methyl-1H-indole

HRID 2268151Notes

Reaction equation

HRID 2268151 reaction equation
[C:1](=O)(OC)OC.N1C2C(=CC=CC=2)C=C1.[CH3:16][O:17][C:18]1[CH:19]=[C:20]2[C:24](=[CH:25][CH:26]=1)[NH:23][CH:22]=[CH:21]2>>[CH3:1][N:23]1[C:24]2[C:20](=[CH:19][C:18]([O:17][CH3:16])=[CH:26][CH:25]=2)[CH:21]=[CH:22]1

Participants

4

Reactant 3

HCID 798IndoleHCID 12021Dimethyl Carbonate2×HCID 138725-Methoxyindole

Product 1

HCID 8198645-methoxy-1-methyl-1H-indole

Procedure

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.

Workup

  1. customfor 5 hours

Sources & evidence

ORD record
ord-93eb2cb644224b91a5b458924660ae14
Source dataset
uspto-grants-2001_12
Patent number
US06326501B1

Reaction notes

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