Hydrogen Peroxide → 6-Methoxyquinoline N-oxide

HRID 55830

Reaktionsgleichung

Reaktionsgleichung von HRID 55830
[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

Komponenten

5

Edukt 3

HCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 148606-Methoxyquinoline

Produkt 1

HCID 2538216-Methoxyquinoline N-oxideAusbeute 55 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

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.

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-6ae501403e814ff08189ae26dd832c3f
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09433618B2

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