Aniline → N,N-Dimethylaniline

HRID 1179206Notes

Reaction equation

HRID 1179206 reaction equation
N[C:2]1[CH:7]=[CH:6]C=[CH:4][CH:3]=1.CI.C(=O)([O-])[O-].[K+].[K+].C(OCC)(=O)C.[CH3:22][N:23]([CH3:26])[CH:24]=O>>[CH3:22][N:23]([CH3:26])[C:24]1[CH:6]=[CH:7][CH:2]=[CH:3][CH:4]=1

Participants

6

Reactant 5

HCID 6115AnilineHCID 6228DimethylformamideHCID 6328Methyl iodideHCID 8857Ethyl AcetateHCID 11430Potassium Carbonate

Product 1

HCID 949N,N-Dimethylaniline

Procedure

The aniline derivative (1.4 g, 7.3 mmol) obtained in Step 1 was dissolved in dimethylformamide (50 ml), methyl iodide (1.4 ml, 22 mmol) and potassium carbonate (3.0 g, 22 mmol) were added, and the mixture was stirred overnight. A treatment according to a conventional method using ethyl acetate as an extraction solvent gave a crude product, which was successively purified by silica gel column chromatography to give a dimethylaniline derivative (1.1 g, 5.0 mmol).

Workup

  1. customgave a crude product, which
  2. customwas successively purified by silica gel column chromatography

Sources & evidence

ORD record
ord-dce4b4e567e842268b2c1c26446cd5f6
Source dataset
uspto-grants-2007_10
Patent number
US07279484B2

Reaction notes

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