trans-3-(3-Pyridyl)acrylic acid → (E)-N-(3-hydroxyphenethyl)-3-(3-pyridyl)-2-propenoic acid amide

HRID 428132

Reaction equation

HRID 428132 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3](/[CH:7]=[CH:8]/[C:9]([OH:11])=O)[CH:2]=1.Br.[OH:13][C:14]1[CH:15]=[C:16]([CH:20]=[CH:21][CH:22]=1)[CH2:17][CH2:18][NH2:19]>ClCCl.C(N(CC)CC)C.C(Cl)(=O)C(C)(C)C>[OH:13][C:14]1[CH:15]=[C:16]([CH:20]=[CH:21][CH:22]=1)[CH2:17][CH2:18][NH:19][C:9](=[O:11])/[CH:8]=[CH:7]/[C:3]1[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=1

Participants

6

Reactant 2

HCID 776396trans-3-(3-Pyridyl)acrylic acidHCID 227178563-(2-Aminoethyl)phenol hydrobromide

Product 1

HCID 23067308(E)-N-(3-hydroxyphenethyl)-3-(3-pyridyl)-2-propenoic acid amideYield 78.1%

Reagents, catalysts & solvents 3

HCID 6344DichloromethaneSolventHCID 8471TriethylamineSolventHCID 62493Pivaloyl chlorideSolvent

Procedure

To a solution of trans-3-(3-pyridyl)acrylic acid (179 g) in dichloromethane (4.8 L), triethylamine (584 ml) and pivaloyl chloride (148 ml) were sequentially added under ice-cooling and stirring and stirred for 15 minutes. Subsequently, 3-hydroxyphenethylamine hydrobromide (263 g) was added at the same temperature and stirred for 2 hours. After the solvent was distilled out under reduced pressure, water was added to the residue and the precipitated crystal was filtered, washed with water and recrystallized in ethanol to yield the titled compound (251.4 g, 78%).

Workup

  1. temperaturecooling
  2. stirringstirred for 15 minutes
  3. stirringstirred for 2 hours
  4. distillationAfter the solvent was distilled out under reduced pressure, water
  5. additionwas added to the residue
  6. filtrationthe precipitated crystal was filtered
  7. washwashed with water
  8. customrecrystallized in ethanol

Sources & evidence

ORD record
ord-30bbc6d9862246738c5adb93bfdae549
Source dataset
uspto-grants-2001_11
Patent number
US06313153B1

Linked notes

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