Water → 1-Methyl-6-nitro-1H-indole

HRID 1004202Notes

Reaction equation

HRID 1004202 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].[CH3:15]I.O>CN(C)C=O>[CH3:15][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

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 785026-Nitro-1H-indole

Product 1

HCID 106073591-Methyl-6-nitro-1H-indoleYield 77.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a slurry of 0.33 g (8.3 mmol) of NaH (60% dispersion in oil) in 30 ml of dried dimethylformamide ("DMF"), was added 0.973 g (6.00 mmol) of commercially available (Lancaster, Windham, N.H.) 6-nitro-IH-indole (1) at 0-5° C. over a period of 10 minutes. After 1 hour stirring at the same temperature, 0.75 ml (12.1 mmol) of methyl iodide was added and the mixture was stirred at the same temperature for 30 minutes, then at room temperature for 1 hour, poured into ice and water and extracted with ethyl acetate. The organic phase was washed with brine, dried over MgSO4, and concentrated to yield 0.814 g (77.5%) of 1-methyl-6-nitro-1H-indole (2) as a yellow solid. This material was used without purification.

Workup

  1. additionwas added
  2. waitat room temperature for 1 hour
  3. extractionextracted with ethyl acetate
  4. washThe organic phase was washed with brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-7480797b854c4c8a81f686ae71c583bb
Source dataset
uspto-grants-2000_04
Patent number
US06048887

Reaction notes

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