Methyl iodide → 4-Methoxy-1H-indole

HRID 430778Notes

Reaction equation

HRID 430778 reaction equation
[OH-].[K+].[OH:3][C:4]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:5]=1[CH:6]=[CH:7][NH:8]2.[CH3:13]I>CN(C=O)C>[CH3:13][O:3][C:4]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:5]=1[CH:6]=[CH:7][NH:8]2

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 14797Potassium Hydroxide2×HCID 754211H-indol-4-ol

Product 1

HCID 1383634-Methoxy-1H-indoleYield 61%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Potassium hydroxide (2.12 g) was added to 4-hydroxyindole (4.99 g) in DMF (100 ml) and the mixture was stirred at room temperature for 30 minutes. Methyl iodide (2.80 ml) was added to the mixture and the resultant was stirred at room temperature for 150 minutes. Since the reaction had not been completed, potassium hydroxide (0.64 g) was added and the mixture was stirred at room temperature for 5 hours. The solvent was removed under reduced pressure and water (20 ml) was added to the residue, followed by extraction with ether (3×30 ml). The organic layers were washed with saturated brine, and dried over sodium sulfate. After removing solids by filtration, the solvent was removed under reduced pressure and the obtained crude product was purified by silica gel column chromatography to obtain the desired product (3.38 g, yield: 61%).

Workup

  1. stirringthe resultant was stirred at room temperature for 150 minutes
  2. stirringthe mixture was stirred at room temperature for 5 hours
  3. customThe solvent was removed under reduced pressure and water (20 ml)
  4. additionwas added to the residue
  5. extractionfollowed by extraction with ether (3×30 ml)
  6. washThe organic layers were washed with saturated brine
  7. dry with materialdried over sodium sulfate
  8. customAfter removing solids
  9. filtrationby filtration
  10. customthe solvent was removed under reduced pressure
  11. customthe obtained crude product
  12. customwas purified by silica gel column chromatography

Sources & evidence

ORD record
ord-35edd2ecff4f4583b83d4198869a93ba
Source dataset
uspto-grants-2001_11
Patent number
US06323235B1

Reaction notes

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