Acetaminophen → Acetamide, N-[4-(2-pyridinyloxy)phenyl]-

HRID 1975742Notes

Reaction equation

HRID 1975742 reaction equation
[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]

Participants

5

Reactant 3

HCID 1983AcetaminophenHCID 79732-BromopyridineHCID 11430Potassium Carbonate

Product 1

HCID 23274470Acetamide, N-[4-(2-pyridinyloxy)phenyl]-

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-46eefa56808e424ea3720d9411ab6f1e
Source dataset
uspto-grants-1994_02
Patent number
US05288743

Reaction notes

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