Reaktion #607452

Reaktionsgleichung

Xanthine Adenosine

3-Nitro-4-hydroxyquinoline

3-nitro-4-hydroxyquinoline

phosphorus oxychloride

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Compound 6

3-nitro-4-chloroquinoline

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe mixture was refluxed for 30 minutes
2. 2
   TemperaturAfter cooling the solvent
3. 3
   workup.ADDITIONwas poured
4. 4
   Sonstigeover crushed ice
5. 5
   workup.STIRRINGwhile stirring
6. 6
   SonstigeAfter 1 hour the solid that was formed
7. 7
   Filtrationwas filtered off
8. 8
   Waschenwashed with cold water
9. 9
   workup.DISSOLUTIONdissolved in ethyl acetate
10. 10
    ExtraktionThe solution was extracted with ice-cold NaOH (1 M) till pH=8-9
11. 11
    Trocknendried over MgSO4
12. 12
    SonstigeThe solvent was evaporated
13. 13
    Sonstigethe residue was dried

Vorschrift

Compound 6 was prepared as described elsewhere [Van Galen, P. J. M. et. al. 1-H-imidazo[4,5-c]quinolin-4-amines: Novel Non-Xanthine Adenosine Antagonists. J. Med. Chem. 1991, 34, 1202-1206]. In brief, 3-Nitro-4-hydroxyquinoline 5 (5.7 g, 30 mmol) was added to phosphorus oxychloride (70.0 g, 41.2 ml, 450 mmol) with stirring. The mixture was refluxed for 30 minutes. After cooling the solvent was poured over crushed ice while stirring. After 1 hour the solid that was formed was filtered off, washed with cold water and dissolved in ethyl acetate. The solution was extracted with ice-cold NaOH (1 M) till pH=8-9 and dried over MgSO4. The solvent was evaporated and the residue was dried. Yield: 5.05 g (81%). Mp.: 118°-119° C. 1H NMR (DMSO-d6): δ 7.94-8.11 (m, 2H, Ar); 8.25 (d, 1H, J=8.0 Hz, Ar); 8.47 (d, 1H, J=9.5 Hz, Ar); 9.42 (s, 1H, Ar).

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