Reacción #607456

Ecuación de reacción

toluene

phosphorus oxychloride

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

→

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

Disolventes

dimethylformamide

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturawas cooled in an ice-bath
2. 2
   TemperaturaSubsequently the solution was heated to 100° C. on a steam bath for 30 minutes
3. 3
   TemperaturaUpon cooling
4. 4
   Otrothe solvent was evaporated
5. 5
   workup.ADDITIONthe resulting syrup was poured
6. 6
   Otroover crushed ice
7. 7
   workup.STIRRINGwhile stirring
8. 8
   TemperaturaThe mixture was then warmed to room temperature
9. 9
   workup.WAITAfter 2 hours
10. 10
    Otrothe solid that was formed
11. 11
    Filtraciónwas filtered off
12. 12
    Lavadowashed with water and diisopropylether
13. 13
    Otrosubsequently dried

Procedimiento

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.

Fuente