Methyl iodide → 5-methoxy-1-methyl-1H-indole

HRID 1017588

Reaction equation

HRID 1017588 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH:7]=[CH:6]2.[OH-].[K+].[CH3:14]I>CN(C=O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[N:8]([CH3:14])[CH:7]=[CH:6]2

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 138725-MethoxyindoleHCID 14797Potassium Hydroxide

Product 1

HCID 8198645-methoxy-1-methyl-1H-indoleYield 82.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 5-methoxyindole (1 g, 6.8 mmol) in 8 mL of DMF were added potassium hydroxide (0.92 g, 2.4 eq.) and methyl iodide (1 mL, 16 mmol). The resulting mixture was stirred at room temperature overnight. After removing volatile, the residue was diluted with EtOAc and washed with water (4×). The organic layer was dried and concentrated to afford 0.9 g (82%) 5-methoxy-1-methylindole. MS (EI): (M++1) 162.

Workup

  1. customAfter removing volatile
  2. additionthe residue was diluted with EtOAc
  3. washwashed with water (4×)
  4. customThe organic layer was dried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-a42b9acf5e5147af8e98fb0c35a46f67
Source dataset
uspto-grants-2002_11
Patent number
US06479490B2

Linked notes

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