Réaction #607452

Équation de réaction

Xanthine Adenosine

3-Nitro-4-hydroxyquinoline

3-nitro-4-hydroxyquinoline

phosphorus oxychloride

→

Compound 6

3-nitro-4-chloroquinoline

Conditions de réaction

Traitement

1. 1
   TempératureThe mixture was refluxed for 30 minutes
2. 2
   TempératureAfter cooling the solvent
3. 3
   workup.ADDITIONwas poured
4. 4
   Autreover crushed ice
5. 5
   workup.STIRRINGwhile stirring
6. 6
   AutreAfter 1 hour the solid that was formed
7. 7
   Filtrationwas filtered off
8. 8
   Lavagewashed with cold water
9. 9
   workup.DISSOLUTIONdissolved in ethyl acetate
10. 10
    ExtractionThe solution was extracted with ice-cold NaOH (1 M) till pH=8-9
11. 11
    Séchagedried over MgSO4
12. 12
    AutreThe solvent was evaporated
13. 13
    Autrethe residue was dried

Mode opératoire

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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