反应 #607452

反应方程式

Xanthine Adenosine

3-Nitro-4-hydroxyquinoline

3-nitro-4-hydroxyquinoline

phosphorus oxychloride

→

Compound 6

3-nitro-4-chloroquinoline

反应条件

后处理

1. 1
   温度The mixture was refluxed for 30 minutes
2. 2
   温度After cooling the solvent
3. 3
   workup.ADDITIONwas poured
4. 4
   其他over crushed ice
5. 5
   workup.STIRRINGwhile stirring
6. 6
   其他After 1 hour the solid that was formed
7. 7
   过滤was filtered off
8. 8
   洗涤washed with cold water
9. 9
   workup.DISSOLUTIONdissolved in ethyl acetate
10. 10
    萃取The solution was extracted with ice-cold NaOH (1 M) till pH=8-9
11. 11
    干燥dried over MgSO4
12. 12
    其他The solvent was evaporated
13. 13
    其他the residue was dried

实验过程

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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