Dimethylformamide → HCID 21072939, compound

HRID 1373237Notes

Reaction equation

HRID 1373237 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:4][CH:3]=1.Br[CH2:15][CH2:16][CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19].C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>O>[CH2:12]([O:11][C:9]([CH2:8][C:5]1[CH:4]=[CH:3][C:2]([NH:1][CH2:15][CH2:16][CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])=[CH:7][CH:6]=1)=[O:10])[CH3:13]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 76300Ethyl 4-bromobutyrateHCID 225219p-Aminophenylacetic acid ethyl ester

Product 1

HCID 21072939HCID 21072939, compoundYield 74.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of ethyl 4-aminophenylacetate (2.0 g, 11 mmols), ethyl 4-bromobutanoate (8.7 g, 45 mmols), potassium carbonate (2.3 g, 17 mmols) and N,N-dimethylformamide (50 ml) was stirred at 60° C. for 24 hours. The reaction mixture was cooled, then poured into water, and extracted with ethyl acetate. The extract was washed with water and brine, and then dried with anhydrous magnesium sulfate. This was concentrated under reduced pressure, and the residue was purified through silica gel column chromatography to give an oil of ethyl 4-[4-(ethoxycarbonylmethyl)phenyl]aminobutanoate (2.4 g, 74%).

Workup

  1. temperatureThe reaction mixture was cooled
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed with water and brine
  4. dry with materialdried with anhydrous magnesium sulfate
  5. concentrationThis was concentrated under reduced pressure
  6. customthe residue was purified through silica gel column chromatography

Sources & evidence

ORD record
ord-73e8f52875e64d0fbdecb4a1a216ce93
Source dataset
uspto-grants-2007_01
Patent number
US07160887B1

Reaction notes

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