Water → 1-Methyl-6-nitro-1H-indole

HRID 1510330Notes

Reaction equation

HRID 1510330 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.C(OCC)(=O)C>[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

7

Reactant 4

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

Product 1

HCID 106073591-Methyl-6-nitro-1H-indole

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

4 g 6-nitro-1H-indole are added batchwise at 0° C. to 800 mg sodium hydride (60% in mineral oil) in 20 mg dimethylformamide. The mixture is stirred for 10 minutes, then 1.86 ml methyl iodide are added dropwise and the mixture is left overnight to come up to ambient temperature. Then it is divided between water and ethyl acetate, the aqueous phase is extracted with ethyl acetate and the combined organic phases are washed with saturated sodium chloride solution. After drying with magnesium sulphate the solvents are eliminated in vacuo.

Workup

  1. waitthe mixture is left overnight
  2. customto come up to ambient temperature
  3. extractionthe aqueous phase is extracted with ethyl acetate
  4. washthe combined organic phases are washed with saturated sodium chloride solution
  5. dry with materialAfter drying with magnesium sulphate the solvents

Sources & evidence

ORD record
ord-3d15c6af41fd44b18adaa60201605f77
Source dataset
uspto-grants-2012_07
Patent number
US08211923B2

Reaction notes

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