Reaktion #7602

Reaktionsgleichung

Aluminium trichloride

4-chloro-7-methoxycinnoline

→

4-chloro-7-hydroxycinnoline

Ausbeute 53.6%

Lösungsmittel

benzene

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturthe mixture was heated
2. 2
   Temperaturat reflux for 1 hour
3. 3
   SonstigeThe solvent was removed by evaporation
4. 4
   Sonstigethe residue was partitioned between ice/water and ethyl acetate
5. 5
   workup.ADDITIONAqueous saturated sodium chloride solution was added
6. 6
   Sonstigethe organic layer was separated
7. 7
   WaschenThe organic layer was washed with brine
8. 8
   Trocknendried (MgSO4)
9. 9
   Sonstigethe solvent removed by evaporation
10. 10
    SonstigeThe residue was triturated with ether
11. 11
    Sonstigecollected
12. 12
    Filtrationfiltered
13. 13
    Sonstigedried under vacuum

Vorschrift

Aluminium trichloride (2.6 g, 19 mmol) was added in portions to a suspension of 4-chloro-7-methoxycinnoline (0.9 g, 3.8 mmol), (J. Chem. Soc. 1955, 2100), in benzene (15 ml) and the mixture was heated at reflux for 1 hour. The solvent was removed by evaporation and the residue was partitioned between ice/water and ethyl acetate. Aqueous saturated sodium chloride solution was added and the organic layer was separated. The organic layer was washed with brine, dried (MgSO4) and the solvent removed by evaporation. The residue was triturated with ether, collected, filtered and dried under vacuum to give 4-chloro-7-hydroxycinnoline (368 mg, 53%).

Quelle