Methyl iodide → 1,3-Dimethylindole

HRID 2097187Notes

Reaction equation

HRID 2097187 reaction equation
[H-].[Na+].[CH3:3][C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[NH:6][CH:5]=1.I[CH3:14]>CN(C=O)C>[CH3:14][N:6]1[C:7]2[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:4]([CH3:3])=[CH:5]1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 6736SkatoleHCID 24758Sodium hydride

Product 1

HCID 701301,3-DimethylindoleYield 59%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (600 mg, 16.6 mmol) was added to a solution of 3-methylindole (2 g, 15.2 mmol) in DMF (10 mL). The mixture was stirred for 30 min and iodomethane was added in one portion. The mixture was cooled in an icebath and left to warm to rt overnight. The mixture was evaporated and the residue dissolved in ethyl acetate. The solution was washed with water and brine, dried over magnesium sulfate and evaporated. The crude reaction was chromatographed over silica gel eluting with hexane and ethyl acetate/hexane (20 and 50%) to afford the title compound (1.3 g, 59%). 1H NMR (400 MHz, CDCl3) δ 7.46 (d, J=8 Hz, 1H), 7.34 (d, J=8 Hz, 1H), 7.12 (t, J=7.8 Hz, 1H), 7.06 (s, 1H), 7.00 (t, J=7.6 Hz, 1H), 3.70 (s, 3H), 2.23 (s, 3H)

Workup

  1. temperatureThe mixture was cooled in an icebath
  2. waitleft
  3. customThe mixture was evaporated
  4. dissolutionthe residue dissolved in ethyl acetate
  5. washThe solution was washed with water and brine
  6. dry with materialdried over magnesium sulfate
  7. customevaporated
  8. customThe crude reaction
  9. customwas chromatographed over silica gel eluting with hexane and ethyl acetate/hexane (20 and 50%)

Sources & evidence

ORD record
ord-357a0ad6f42543ca9aa976841e6d77eb
Source dataset
uspto-grants-2013_05
Patent number
US08450307B2

Reaction notes

Loading…