Réaction #607456

Équation de réaction

toluene

phosphorus oxychloride

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

→

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

Solvants

dimethylformamide

Conditions de réaction

Traitement

1. 1
   Températurewas cooled in an ice-bath
2. 2
   TempératureSubsequently the solution was heated to 100° C. on a steam bath for 30 minutes
3. 3
   TempératureUpon cooling
4. 4
   Autrethe solvent was evaporated
5. 5
   workup.ADDITIONthe resulting syrup was poured
6. 6
   Autreover crushed ice
7. 7
   workup.STIRRINGwhile stirring
8. 8
   TempératureThe mixture was then warmed to room temperature
9. 9
   workup.WAITAfter 2 hours
10. 10
    Autrethe solid that was formed
11. 11
    Filtrationwas filtered off
12. 12
    Lavagewashed with water and diisopropylether
13. 13
    Autresubsequently dried

Mode opératoire

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