Methyl iodide → 1-Methyl-5-nitro-1H-indole-3-carbaldehyde

HRID 618105Notes

Reaction equation

HRID 618105 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][CH:8]=[C:7]2[CH:13]=[O:14])([O-:3])=[O:2].[C:15](=O)([O-])[O-].[K+].[K+].CI>CN(C)C=O>[CH3:15][N:9]1[C:10]2[C:6](=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:12][CH:11]=2)[C:7]([CH:13]=[O:14])=[CH:8]1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 2460395-nitro-1H-indole-3-carbaldehyde

Product 1

HCID 128715121-Methyl-5-nitro-1H-indole-3-carbaldehydeYield 92.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

5-Nitroindole-3-carboxaldehyde (2 g) was dissolved in N,N-dimethylformamide (40 ml), and potassium carbonate (4.0 g) and methyl iodide (5 ml) were added thereto, followed by stirring at 60° C. for 24 hours. The reaction solution was subjected to partitioning with chloroform, methanol and water, and the organic layer was dried over magnesium sulfate. After concentration under reduced pressure, the residue was rinsed with ethyl acetate to give 1-methyl-5-nitroindole-3-carboxaldehyde (Compound III-2, 1.99 g).

Workup

  1. customto partitioning with chloroform, methanol and water
  2. dry with materialthe organic layer was dried over magnesium sulfate
  3. concentrationAfter concentration under reduced pressure
  4. washthe residue was rinsed with ethyl acetate

Sources & evidence

ORD record
ord-9b7c0d8c56f747a5a79040795b1e06b1
Source dataset
uspto-grants-1999_09
Patent number
US05952355

Reaction notes

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