Methyl iodide → 1-methyl-1H-indole-7-carbaldehyde

HRID 1362048Notes

Reaction equation

HRID 1362048 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][C:8]=2[CH:10]=[O:11])[CH:3]=[CH:2]1.[H-].[Na+].CI.[C:16](OCC)(=O)C>CN(C=O)C>[CH3:16][N:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][C:8]=2[CH:10]=[O:11])[CH:3]=[CH:2]1

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 2734629Indole-7-carboxaldehyde

Product 1

HCID 110409791-methyl-1H-indole-7-carbaldehyde

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of indole-7-carboxaldehyde (500 mg, 3.45 mmol) in DMF (8 mL) was added sodium hydride (152 mg of 60% dispersion in oil, 3.8 mmol). The mixture was stirred for 30 mins. Methyl iodide (0.98 g, 6.9 mmol) was then added and the mixture was stirred for 2 hrs. Ethyl acetate (200 mL) was added and solution was washed with H2O (3×20 mL) and brine (25 mL) dried over MgSO4 and concentrated to afford N-methylindole-7-carboxaldehyde as a brown oil which was used without further purification.

Workup

  1. stirringthe mixture was stirred for 2 hrs
  2. washsolution was washed with H2O (3×20 mL) and brine (25 mL)
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-a998fb55a429456aa69f41c2800f5c96
Source dataset
uspto-grants-2011_02
Patent number
US07879872B2

Reaction notes

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