Reaktion #84108

Reaktionsgleichung

NaOH

6-methoxyquinoline

H2O2

→

6-methoxyquinoline 1-oxide

Ausbeute 55.0%

Lösungsmittel

AcOH

Reaktionsbedingungen

Aufarbeitung

1. 1
   Extraktionextracted with CH2Cl2 (200 mL)
2. 2
   Waschenthe combined organic layer was washed with brine (50 mL)
3. 3
   Trocknendried over Na2SO4
4. 4
   Filtrationfiltered
5. 5
   Einengenconcentrated
6. 6
   Sonstigeto give the crude product, which
7. 7
   Sonstigewas purified by silica gel column (EtOAc/MeOH=10/1)

Vorschrift

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.

Quelle