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

HRID 1920500Notes

Reaction equation

HRID 1920500 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-f184d4a64e9649279295510d7f5df796
Source dataset
uspto-grants-2012_05
Patent number
US08168827B2

Reaction notes

Loading…