반응 #607452

반응 방정식

Xanthine Adenosine

3-Nitro-4-hydroxyquinoline

3-nitro-4-hydroxyquinoline

phosphorus oxychloride

→

Compound 6

3-nitro-4-chloroquinoline

반응 조건

후처리

1. 1
   온도The mixture was refluxed for 30 minutes
2. 2
   온도After cooling the solvent
3. 3
   workup.ADDITIONwas poured
4. 4
   기타over crushed ice
5. 5
   workup.STIRRINGwhile stirring
6. 6
   기타After 1 hour the solid that was formed
7. 7
   여과was filtered off
8. 8
   세척washed with cold water
9. 9
   workup.DISSOLUTIONdissolved in ethyl acetate
10. 10
    추출The solution was extracted with ice-cold NaOH (1 M) till pH=8-9
11. 11
    건조dried over MgSO4
12. 12
    기타The solvent was evaporated
13. 13
    기타the residue was dried

실험 절차

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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