Реакция #607456

Уравнение реакции

toluene

phosphorus oxychloride

1H-imidazo[4,5-c]quinolin-5-oxide

→

4-chloro-1H-imidazo[4,5-c]quinoline

Растворители

dimethylformamide

Условия реакции

Обработка

1. 1
   Температураwas cooled in an ice-bath
2. 2
   ТемператураSubsequently the solution was heated to 100° C. on a steam bath for 30 minutes
3. 3
   ТемператураUpon cooling
4. 4
   Другоеthe solvent was evaporated
5. 5
   workup.ADDITIONthe resulting syrup was poured
6. 6
   Другоеover crushed ice
7. 7
   workup.STIRRINGwhile stirring
8. 8
   ТемператураThe mixture was then warmed to room temperature
9. 9
   workup.WAITAfter 2 hours
10. 10
    Другоеthe solid that was formed
11. 11
    Фильтрацияwas filtered off
12. 12
    Промывкаwashed with water and diisopropylether
13. 13
    Другоеsubsequently dried

Методика

A mixture of toluene (0.45 ml/mmol) and dimethylformamide (0.90 ml/mmol) was cooled in an ice-bath and phosphorus oxychloride (2.6 eq.) was added. After 10 minutes the appropriate 1H-imidazo[4,5-c]quinolin-5-oxide was added and the solution was stirred at room temperature for 10 minutes. Subsequently the solution was heated to 100° C. on a steam bath for 30 minutes. Upon cooling, the solvent was evaporated and the resulting syrup was poured over crushed ice while stirring. The mixture was then warmed to room temperature and carefully adjusted to pH 6-7 with solid NaHCO3. After 2 hours, the solid that was formed was filtered off, washed with water and diisopropylether and subsequently dried.

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