反応 #607452

反応方程式

Xanthine Adenosine

3-Nitro-4-hydroxyquinoline

3-nitro-4-hydroxyquinoline

phosphorus oxychloride

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Compound 6

3-nitro-4-chloroquinoline

反応条件

後処理

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
   その他over crushed ice
5. 5
   workup.STIRRINGwhile stirring
6. 6
   その他After 1 hour the solid that was formed
7. 7
   ろ過was filtered off
8. 8
   洗浄washed with cold water
9. 9
   workup.DISSOLUTIONdissolved in ethyl acetate
10. 10
    抽出The solution was extracted with ice-cold NaOH (1 M) till pH=8-9
11. 11
    乾燥dried over MgSO4
12. 12
    その他The solvent was evaporated
13. 13
    その他the residue was dried

実験手順

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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