Methyl iodide → 1-Methyl-4-nitro-1H-indole

HRID 1728594Notes

Reaction equation

HRID 1728594 reaction equation
[H-].[Na+].[N+:3]([C:6]1[CH:14]=[CH:13][CH:12]=[C:11]2[C:7]=1[CH:8]=[CH:9][NH:10]2)([O-:5])=[O:4].I[CH3:16]>CN(C)C=O>[CH3:16][N:10]1[C:11]2[C:7](=[C:6]([N+:3]([O-:5])=[O:4])[CH:14]=[CH:13][CH:12]=2)[CH:8]=[CH:9]1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 1457664-Nitro-1H-indole

Product 1

HCID 131680671-Methyl-4-nitro-1H-indoleYield 92%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

To a stirred suspension of sodium hydride (0.14 g; 3.41 mM) in dimethylformamide (10 ml) at 0° C. under nitrogen was added 4-nitroindole (0.5 g; 3.1 mM) in dimethylformamide. After stirring for 0.5 h, iodomethane (0.21 ml; 3.41 mM) in dimethylformamide (1 ml) was added, and stirring was continued for 1 h. The reaction mixture was then quenched with water, and poured onto excess water with stirring. Filtration afforded the title compound (0.5 g; 92%).

Workup

  1. stirringstirring
  2. waitwas continued for 1 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-6ccadd5516884e35af0a36fe1ca20618
Source dataset
uspto-grants-1994_07
Patent number
US05328922

Reaction notes

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