Water → N-Methyl-5-benzyloxyindole

HRID 1280074Notes

Reaction equation

HRID 1280074 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+].O.[CH3:21]N(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

5

Reactant 4

HCID 962WaterHCID 6228DimethylformamideHCID 146245-BenzyloxyindoleHCID 24758Sodium hydride

Product 1

HCID 259196N-Methyl-5-benzyloxyindoleYield 90%

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. lodomethane (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. additionwas added
  3. stirringthe reaction stirred at room temperature overnight
  4. filtrationthe precipitated solid collected by filtration
  5. washAfter washing with water
  6. customdrying

Sources & evidence

ORD record
ord-6e93bcacbdb74392b896b68b69893681
Source dataset
uspto-grants-2002_09
Patent number
US06448281B1

Reaction notes

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