تفاعل #607452

معادلة التفاعل

Xanthine Adenosine

3-Nitro-4-hydroxyquinoline

3-nitro-4-hydroxyquinoline

phosphorus oxychloride

→

Compound 6

3-nitro-4-chloroquinoline

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةThe mixture was refluxed for 30 minutes
2. 2
   درجة الحرارةAfter cooling the solvent
3. 3
   workup.ADDITIONwas poured
4. 4
   أخرىover crushed ice
5. 5
   workup.STIRRINGwhile stirring
6. 6
   أخرىAfter 1 hour the solid that was formed
7. 7
   ترشيحwas filtered off
8. 8
   غسيلwashed with cold water
9. 9
   workup.DISSOLUTIONdissolved in ethyl acetate
10. 10
    استخلاصThe solution was extracted with ice-cold NaOH (1 M) till pH=8-9
11. 11
    تجفيفdried over MgSO4
12. 12
    أخرىThe solvent was evaporated
13. 13
    أخرىthe residue was dried

الإجراء التجريبي

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).

المصدر