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

HRID 428132

反応式

HRID 428132 の反応式
[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

参加物

6

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 6344Dichloromethane溶媒HCID 8471Triethylamine溶媒HCID 62493Pivaloyl chloride溶媒

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-30bbc6d9862246738c5adb93bfdae549
出典データセット
uspto-grants-2001_11
特許番号
US06313153B1

関連ノート

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