Reacción #607452

Ecuación de reacción

Xanthine Adenosine

3-Nitro-4-hydroxyquinoline

3-nitro-4-hydroxyquinoline

phosphorus oxychloride

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Compound 6

3-nitro-4-chloroquinoline

Condiciones de reacción

Tratamiento posterior

1. 1
   TemperaturaThe mixture was refluxed for 30 minutes
2. 2
   TemperaturaAfter cooling the solvent
3. 3
   workup.ADDITIONwas poured
4. 4
   Otroover crushed ice
5. 5
   workup.STIRRINGwhile stirring
6. 6
   OtroAfter 1 hour the solid that was formed
7. 7
   Filtraciónwas filtered off
8. 8
   Lavadowashed with cold water
9. 9
   workup.DISSOLUTIONdissolved in ethyl acetate
10. 10
    ExtracciónThe solution was extracted with ice-cold NaOH (1 M) till pH=8-9
11. 11
    Secadodried over MgSO4
12. 12
    OtroThe solvent was evaporated
13. 13
    Otrothe residue was dried

Procedimiento

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).

Fuente