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

HRID 1975742노트

반응식

HRID 1975742 반응식
[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]

참가 물질

5

반응물 3

HCID 1983AcetaminophenHCID 79732-BromopyridineHCID 11430Potassium Carbonate

생성물 1

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

시약·촉매·용매 1

HCID 1049Pyridine용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-46eefa56808e424ea3720d9411ab6f1e
출처 데이터셋
uspto-grants-1994_02
특허 번호
US05288743

반응 노트

불러오는 중…