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

HRID 1975742Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1975742
[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]

Komponenten

5

Edukt 3

HCID 1983AcetaminophenHCID 79732-BromopyridineHCID 11430Potassium Carbonate

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-46eefa56808e424ea3720d9411ab6f1e
Quelldatensatz
uspto-grants-1994_02
Patentnummer
US05288743

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