Methyl chloroacetate → methyl [3-[2-[(E)-3-(3-pyridyl)acryloylamino]ethyl]phenoxy]acetate

HRID 428135Notes

Reaction equation

HRID 428135 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:18]=[CH:19][CH:20]=1)[CH2:5][CH2:6][NH:7][C:8](=[O:17])/[CH:9]=[CH:10]/[C:11]1[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=1.Cl[CH2:22][C:23]([O:25][CH3:26])=[O:24].C(=O)([O-])[O-].[K+].[K+].C(OCC)(=O)C>CN(C)C=O>[N:13]1[CH:14]=[CH:15][CH:16]=[C:11](/[CH:10]=[CH:9]/[C:8]([NH:7][CH2:6][CH2:5][C:4]2[CH:3]=[C:2]([CH:20]=[CH:19][CH:18]=2)[O:1][CH2:22][C:23]([O:25][CH3:26])=[O:24])=[O:17])[CH:12]=1

Participants

6

Reactant 4

HCID 7295Methyl chloroacetateHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 23067308(E)-N-(3-hydroxyphenethyl)-3-(3-pyridyl)-2-propenoic acid amide

Product 1

HCID 20701346methyl [3-[2-[(E)-3-(3-pyridyl)acryloylamino]ethyl]phenoxy]acetateYield 61%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

(E)-N-(3-hydroxyphenethyl)-3-(3-pyridyl)-2-propenoic acid amide (1.07 g, 4.0 mmol) obtained in Example 81 and methyl chloroacetate (0.52 g, 4.8 mmol) were dissolved in dimethylformamide (12 ml) and potassium carbonate (1.66 g, 12 mmol) was added and stirred at 60° C. for 8 hours. After allowing to cool, ethyl acetate was added to the reaction mixture and insoluble materials were filtered out. The filtrate was washed with water and dried over magnesium sulfate. After the solvent was distilled out under reduced pressure, the residue was recrystallized to yield the titled compound (0.83 g, 61%).

Workup

  1. temperatureto cool
  2. filtrationwere filtered out
  3. washThe filtrate was washed with water
  4. dry with materialdried over magnesium sulfate
  5. distillationAfter the solvent was distilled out under reduced pressure
  6. customthe residue was recrystallized

Sources & evidence

ORD record
ord-5b48e717aaf54df0a5f90ef1714b17f2
Source dataset
uspto-grants-2001_11
Patent number
US06313153B1

Reaction notes

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