Hydrogen Peroxide → 6-Methoxyquinoline N-oxide

HRID 55830

반응식

HRID 55830 반응식
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]=[CH:8][CH:7]=[CH:6]2.[OH:13]O.[OH-].[Na+]>CC(O)=O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N+:9]([O-:13])=[CH:8][CH:7]=[CH:6]2

참가 물질

5

반응물 3

HCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 148606-Methoxyquinoline

생성물 1

HCID 2538216-Methoxyquinoline N-oxide수율 55%

시약·촉매·용매 1

HCID 176Acetic Acid용매

반응 조건

온도
70 °C

실험 절차

To a solution of 6-methoxyquinoline (2.00 g, 12.6 mmol) in AcOH (10 mL) was added H2O2 (30% in water, 1.9 mL, 18.9 mmol), the mixture was heated to 70° C. for 21 hours. The mixture was basified with 2M NaOH to pH 8-9 and extracted with CH2Cl2 (200 mL), the combined organic layer was washed with brine (50 mL), dried over Na2SO4, filtered and concentrated to give the crude product, which was purified by silica gel column (EtOAc/MeOH=10/1) to give 6-methoxyquinoline 1-oxide (1.20 g, 55%) as a solid.

후처리

  1. extractionextracted with CH2Cl2 (200 mL)
  2. washthe combined organic layer was washed with brine (50 mL)
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto give the crude product, which
  7. customwas purified by silica gel column (EtOAc/MeOH=10/1)

출처 및 근거

ORD 기록
ord-6ae501403e814ff08189ae26dd832c3f
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09433618B2

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