Water → 1-(1-Methyl-1H-indol-6-yl)ethan-1-one

HRID 442755Notes

Reaction equation

HRID 442755 reaction equation
[H-].[Na+].[C:3]([C:6]1[CH:14]=[C:13]2[C:9]([CH:10]=[CH:11][NH:12]2)=[CH:8][CH:7]=1)(=[O:5])[CH3:4].[CH3:15]I.O>CN(C)C=O>[CH3:15][N:12]1[C:13]2[C:9](=[CH:8][CH:7]=[C:6]([C:3](=[O:5])[CH3:4])[CH:14]=2)[CH:10]=[CH:11]1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 129250701-(1H-Indol-6-yl)ethan-1-one

Product 1

HCID 538738741-(1-Methyl-1H-indol-6-yl)ethan-1-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a slurry of 0.26 g (6.55 mmole) of NaH (60% oil dispersion) in 10 mL of dried N,N-dimethylformamide, a solution of 6-acetylindole (1.04 g, 6.55 mmole) in 5 mL of dried N,N-dimethylformamide was added at 0°-4° C. After 15 min. stirring at the same temperature, 1.45 g (10.1 mmole) of methyl iodide was added. The new mixture was stirred at the same temperature for 1 hour, poured into ice and water and extracted with ethyl acetate. The organic phase was washed with brine, dried over magnesium sulfate and concentrated to give 1-(1-methyl-1H-indol-6-yl)-ethanone after chromatographic purification on a silica gel column.

Workup

  1. additionwas added
  2. extractionextracted with ethyl acetate
  3. washThe organic phase was washed with brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-69798f98d75642fc8100d38e06f551df
Source dataset
uspto-grants-1999_04
Patent number
US05891901

Reaction notes

Loading…