Methyl iodide → 1H-Indole, 1-methyl-5-nitro-

HRID 1728591Notes

Reaction equation

HRID 1728591 reaction equation
[H-].[Na+].[N+:3]([C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][CH:14]=1)[NH:11][CH:10]=[CH:9]2)([O-:5])=[O:4].I[CH3:16]>CN(C)C=O>[CH3:16][N:11]1[C:12]2[C:8](=[CH:7][C:6]([N+:3]([O-:5])=[O:4])=[CH:14][CH:13]=2)[CH:9]=[CH:10]1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 225235-NitroindoleHCID 24758Sodium hydride

Product 1

HCID 1473221H-Indole, 1-methyl-5-nitro-Yield 94%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

To a stirred suspension of sodium hydride (5.0 g; 167 mM) in dimethylformamide (200 ml) at 0° C. under nitrogen was added 5-nitroindole (25 g; 154 mM) in dimethylformamide. After stirring for 0.5 h, iodomethane (10.5 ml; 168 mM) in dimethylformamide (50 ml) was added, and stirring was continued for 2 h. The reaction mixture was then quenched with water, and poured onto excess water with stirring. Filtration afforded the title compound (27.4 g; 94%).

Workup

  1. stirringstirring
  2. waitwas continued for 2 h
  3. customThe reaction mixture was then quenched with water
  4. additionpoured onto excess water
  5. stirringwith stirring
  6. filtrationFiltration

Sources & evidence

ORD record
ord-bb958a7878f74d04ad4999623fdeca34
Source dataset
uspto-grants-1994_07
Patent number
US05328922

Reaction notes

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