Water → N-Methyl-5-benzyloxyindole

HRID 1018250Notes

Reaction equation

HRID 1018250 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[NH:14][CH:13]=[CH:12]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].I[CH3:21].O>CN(C=O)C>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[N:14]([CH3:21])[CH:13]=[CH:12]2)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 146245-BenzyloxyindoleHCID 24758Sodium hydride

Product 1

HCID 259196N-Methyl-5-benzyloxyindoleYield 90%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

5-benzyloxyindole (2.00 g, 8.96 mmol) was dissolved in DMF (20 mL) and the solution cooled in ice. Sodium hydride (60% oil dispersion, 1.2 equivalent, 10.7 mmol, 0.43 g) was added and the mixture stirred for 30 min. Iodomethane (1.2 equivalent, 10.7 mmol, 0.67 mL) was added and the reaction stirred at room temperature overnight. The reaction was then poured into water (150 mL) and the precipitated solid collected by filtration. After washing with water and drying, 5-benzyloxy-1-methylindole (1.913 g, 90% yield) was obtained as a white solid.

Workup

  1. temperaturethe solution cooled in ice
  2. stirringthe reaction stirred at room temperature overnight
  3. filtrationthe precipitated solid collected by filtration
  4. washAfter washing with water
  5. customdrying

Sources & evidence

ORD record
ord-a41d2d2810d3450682645c30522c1678
Source dataset
uspto-grants-2002_11
Patent number
US06479508B1

Reaction notes

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