Acetic Anhydride → 4-(4-(trifluoromethyl)benzyloxy)pyridin-2(1H)-one

HRID 2202842

반응식

HRID 2202842 반응식
[F:1][C:2]([F:19])([F:18])[C:3]1[CH:17]=[CH:16][C:6]([CH2:7][O:8][C:9]2[CH:14]=[CH:13][N+:12]([O-])=[CH:11][CH:10]=2)=[CH:5][CH:4]=1.C(OC(=O)C)(=[O:22])C>>[F:1][C:2]([F:19])([F:18])[C:3]1[CH:17]=[CH:16][C:6]([CH2:7][O:8][C:9]2[CH:14]=[CH:13][NH:12][C:11](=[O:22])[CH:10]=2)=[CH:5][CH:4]=1

참가 물질

3

반응물 2

HCID 7918Acetic AnhydrideHCID 686576494-(4-(Trifluoromethyl)benzyloxy)pyridine 1-oxide

생성물 1

HCID 579504804-(4-(trifluoromethyl)benzyloxy)pyridin-2(1H)-one

실험 절차

A solution of 4-((4-(trifluoromethyl)benzyl)oxy)pyridine 1-oxide (350 mg) in acetic anhydride (6 ml) was heated under reflux for 4 h. The reaction mixture was then cooled to room temperature and concentrated in vacuo. The residue was diluted with MeOH (10 ml) and 2 M NaOH (10 ml), and heated at reflux for 1 h. The reaction mixture was cooled to room temperature and concentrated in vacuo. The residue was diluted with water and extracted with DCM. The DCM layer was concentrated in vacuo and purified by silica gel column chromatography (MeOH/DCM) to give the title compound (110 mg) as an off-white solid.

후처리

  1. temperatureunder reflux for 4 h
  2. concentrationconcentrated in vacuo
  3. additionThe residue was diluted with MeOH (10 ml) and 2 M NaOH (10 ml)
  4. temperatureheated
  5. temperatureat reflux for 1 h
  6. temperatureThe reaction mixture was cooled to room temperature
  7. concentrationconcentrated in vacuo
  8. additionThe residue was diluted with water
  9. extractionextracted with DCM
  10. concentrationThe DCM layer was concentrated in vacuo
  11. custompurified by silica gel column chromatography (MeOH/DCM)

출처 및 근거

ORD 기록
ord-5ade6a1d9ba7468caf5ad965a11d205c
출처 데이터셋
uspto-grants-2016_06
특허 번호
US09365540B2

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