Acetic Anhydride → 3-[2-[[(E)-3-(3-pyridyl)-acryloyl]amino]ethyl]phenyl acetate

HRID 428137Notes

Reaction equation

HRID 428137 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.[C:21](OC(=O)C)(=[O:23])[CH3:22].C(OCC)(=O)C>N1C=CC=CC=1>[C:21]([O:1][C:2]1[CH:20]=[CH:19][CH:18]=[C:4]([CH2:5][CH2:6][NH:7][C:8](=[O:17])/[CH:9]=[CH:10]/[C:11]2[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=2)[CH:3]=1)(=[O:23])[CH3:22]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 8857Ethyl AcetateHCID 23067308(E)-N-(3-hydroxyphenethyl)-3-(3-pyridyl)-2-propenoic acid amide

Product 1

HCID 207013203-[2-[[(E)-3-(3-pyridyl)-acryloyl]amino]ethyl]phenyl acetateYield 82.6%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

(E)-N-(3-hydroxyphenethyl)-3-(3-pyridyl)-2-propenoic acid amide (600 mg, 2.24 mmol) obtained in Example 81 was dissolved in pyridine (4.0 ml) and acetic anhydride (0.40 ml, 4.24 mmol) was added under ice-cooling and stirred at room temperature for 1.5 hours. Ethyl acetate was added to the reaction mixture and the mixture was washed with water and dried over magnesium sulfate. The solvent was distilled out under reduced pressure, and the residue was purified by silica gel column chromatography (methanol:dichloromethane=1:30) and recrystallized to yield the titled compound (574 mg, 82%).

Workup

  1. temperaturecooling
  2. washthe mixture was washed with water
  3. dry with materialdried over magnesium sulfate
  4. distillationThe solvent was distilled out under reduced pressure
  5. customthe residue was purified by silica gel column chromatography (methanol:dichloromethane=1:30)
  6. customrecrystallized

Sources & evidence

ORD record
ord-075f229fb7b94fd3b94221b027df1634
Source dataset
uspto-grants-2001_11
Patent number
US06313153B1

Reaction notes

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