Methyl iodide → 1-Methyl-6-nitro-1H-indole

HRID 1728596Notes

Reaction equation

HRID 1728596 reaction equation
[H-].[Na+].[N+: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])=[O:4].I[CH3:16]>CN(C)C=O>[CH3:16][N:12]1[C:13]2[C:9](=[CH:8][CH:7]=[C:6]([N+:3]([O-:5])=[O:4])[CH:14]=2)[CH:10]=[CH:11]1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 785026-Nitro-1H-indole

Product 1

HCID 106073591-Methyl-6-nitro-1H-indoleYield 94%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

To a solution of sodium hydride (0.27 g; 6.8 mM) in dimethylformamide (4 ml) at 0° C. under nitrogen, was added 6-nitroindole (1 g; 6.2 mM) in dimethylformamide (12 ml). After stirring at room temperature for 0.5 h, iodomethane (0.42 ml; 6.8 mM) in dimethylformamide (1 ml) was added and stirring continued for 1 h. The reaction mixture was then quenched with water, and poured onto excess water with stirring. Filtration afforded the title compound (1.03 g; 94%).

Workup

  1. stirringstirring
  2. waitcontinued 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-0fe61a403df24c539c737035e273620a
Source dataset
uspto-grants-1994_07
Patent number
US05328922

Reaction notes

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