Reaction #607456

Reaction equation

toluene

phosphorus oxychloride

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

→

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

Solvents

dimethylformamide

Conditions

Workup

1. 1
   Temperaturewas cooled in an ice-bath
2. 2
   TemperatureSubsequently the solution was heated to 100° C. on a steam bath for 30 minutes
3. 3
   TemperatureUpon cooling
4. 4
   Otherthe solvent was evaporated
5. 5
   workup.ADDITIONthe resulting syrup was poured
6. 6
   Otherover crushed ice
7. 7
   workup.STIRRINGwhile stirring
8. 8
   TemperatureThe mixture was then warmed to room temperature
9. 9
   workup.WAITAfter 2 hours
10. 10
    Otherthe solid that was formed
11. 11
    Filtrationwas filtered off
12. 12
    Washwashed with water and diisopropylether
13. 13
    Othersubsequently dried

Procedure

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.

Source