Acetaminophen → N-acetyl-4-(pyrid-2-yloxy)aniline

HRID 1975742ノート

反応式

HRID 1975742 の反応式
[C:1]([NH:4][C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][CH:6]=1)(=[O:3])[CH3:2].Br[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=1.C(=O)([O-])[O-].[K+].[K+]>N1C=CC=CC=1>[C:1]([NH:4][C:5]1[CH:10]=[CH:9][C:8]([O:11][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=2)=[CH:7][CH:6]=1)(=[O:3])[CH3:2]

参加物

5

反応物 3

HCID 1983AcetaminophenHCID 79732-BromopyridineHCID 11430Potassium Carbonate

生成物 1

HCID 23274470N-acetyl-4-(pyrid-2-yloxy)aniline

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

実験手順

A solution of 4-acetamidophenol (20.0 g; 132.3 mmol), 2-bromopyridine (41.8 g; 265 mmol), potassium carbonate (28.3 g; 205 mmol) and Cu° (4.2 g; 66 mmol) in 130 mL pyridine was heated at reflux for 2 days. The reaction was cooled to ambient temperature and filtered through celite. The filtrate was diluted with ethyl acetate and washed with water. The extracts were dried over magnesium sulfate and the solvent was removed under reduced pressure. The material was partially purified by flash chromatography (3% methanol in dichloromethane) and then recrystallized from ethyl acetate/hexane to give N-acetyl-4-(pyrid-2-yloxy)aniline.

後処理

  1. temperatureat reflux for 2 days
  2. filtrationfiltered through celite
  3. additionThe filtrate was diluted with ethyl acetate
  4. washwashed with water
  5. dry with materialThe extracts were dried over magnesium sulfate
  6. customthe solvent was removed under reduced pressure
  7. customThe material was partially purified by flash chromatography (3% methanol in dichloromethane)
  8. customrecrystallized from ethyl acetate/hexane

出典と根拠

ORDレコード
ord-46eefa56808e424ea3720d9411ab6f1e
出典データセット
uspto-grants-1994_02
特許番号
US05288743

反応ノート

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