Water → 1-Methyl-6-nitro-1H-indole

HRID 1976720Notes

Reaction equation

HRID 1976720 reaction equation
[N+:1]([C:4]1[CH:12]=[C:11]2[C:7]([CH:8]=[CH:9][NH:10]2)=[CH:6][CH:5]=1)([O-:3])=[O:2].[H-].[Na+].[CH3:15]I.O>CN(C)C=O>[CH3:15][N:10]1[C:11]2[C:7](=[CH:6][CH:5]=[C:4]([N+:1]([O-:3])=[O:2])[CH:12]=2)[CH:8]=[CH:9]1

Participants

6

Reactant 4

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

Product 1

HCID 106073591-Methyl-6-nitro-1H-indoleYield 97%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

A solution of known 6-nitro-1H-indole (5 g, 31 mm) in dimethylformamide (DMF) (50 mL) was cooled to 0° C. and treated with NaH (1 g, 37m). After stirring at 0° C. for two hours, CH3I (2.3 mL, 37 mm) was added, and the reaction was stirred overnight while allowing to warm to room temperature. After pouring into H2O (500 mL), the mixture was extracted with ethyl acetate (EtOAc) (200 mL×4). The combined organic fractions were dried over MgSO4, filtered and evaporated. Purification by flash column chromatography afforded the 1-methyl-6-nitro-1H-indole (5.34 g, 97%).

Workup

  1. stirringthe reaction was stirred overnight
  2. temperatureto warm to room temperature
  3. extractionthe mixture was extracted with ethyl acetate (EtOAc) (200 mL×4)
  4. dry with materialThe combined organic fractions were dried over MgSO4
  5. filtrationfiltered
  6. customevaporated
  7. customPurification by flash column chromatography

Sources & evidence

ORD record
ord-dca0773f19274ec0ac542b3a52caf5e4
Source dataset
uspto-grants-2001_05
Patent number
US06228877B1

Reaction notes

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