Dimethylformamide → Ethyl 4-[ethyl(3-methylphenyl)amino]butanoate

HRID 2100642Notes

Reaction equation

HRID 2100642 reaction equation
[CH2:1]([O:3][C:4](=[O:9])[CH2:5][CH2:6][CH2:7]Br)[CH3:2].C(=O)([O-])[O-].[K+].[K+].CN(C=O)C.[CH2:21]([NH:23][C:24]1[CH:29]=[CH:28][CH:27]=[C:26]([CH3:30])[CH:25]=1)[CH3:22]>C(OCC)(=O)C>[CH2:1]([O:3][C:4](=[O:9])[CH2:5][CH2:6][CH2:7][N:23]([CH2:21][CH3:22])[C:24]1[CH:29]=[CH:28][CH:27]=[C:26]([CH3:30])[CH:25]=1)[CH3:2]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 7603N-ethyl-3-methylanilineHCID 11430Potassium CarbonateHCID 76300Ethyl 4-bromobutyrate

Product 1

HCID 66966695Ethyl 4-[ethyl(3-methylphenyl)amino]butanoate

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
95 °C

Procedure

4-Bromobutyric acid ethyl ester (17.1 ml), potassium carbonate (20.5 g), and DMF (80 ml) were added to N-ethyl-m-toluidine (8 g), and the mixture was stirred at 95° C. for 17 hours. The reaction mixture was diluted with ethyl acetate, washed with water, and dried over magnesium sulfate. The solvent was evaporated, and the residue was purified by silica gel chromatography (hexane-ethyl acetate) to give the title compound (14.1 g).

Workup

  1. washwashed with water
  2. dry with materialdried over magnesium sulfate
  3. customThe solvent was evaporated
  4. customthe residue was purified by silica gel chromatography (hexane-ethyl acetate)

Sources & evidence

ORD record
ord-a6d02ee545174970bed4a06579dfe9e9
Source dataset
uspto-grants-2009_08
Patent number
US07572815B2

Reaction notes

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