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

HRID 428132

반응식

HRID 428132 반응식
[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

참가 물질

6

반응물 2

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

생성물 1

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

시약·촉매·용매 3

HCID 6344Dichloromethane용매HCID 8471Triethylamine용매HCID 62493Pivaloyl chloride용매

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-30bbc6d9862246738c5adb93bfdae549
출처 데이터셋
uspto-grants-2001_11
특허 번호
US06313153B1

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