Реакция #607452

Уравнение реакции

Xanthine Adenosine

3-Nitro-4-hydroxyquinoline

3-nitro-4-hydroxyquinoline

phosphorus oxychloride

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Compound 6

3-nitro-4-chloroquinoline

Условия реакции

Обработка

1. 1
   ТемператураThe mixture was refluxed for 30 minutes
2. 2
   ТемператураAfter cooling the solvent
3. 3
   workup.ADDITIONwas poured
4. 4
   Другоеover crushed ice
5. 5
   workup.STIRRINGwhile stirring
6. 6
   ДругоеAfter 1 hour the solid that was formed
7. 7
   Фильтрацияwas filtered off
8. 8
   Промывкаwashed with cold water
9. 9
   workup.DISSOLUTIONdissolved in ethyl acetate
10. 10
    ЭкстракцияThe solution was extracted with ice-cold NaOH (1 M) till pH=8-9
11. 11
    Сушкаdried over MgSO4
12. 12
    ДругоеThe solvent was evaporated
13. 13
    Другоеthe residue was dried

Методика

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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