Phosphorus oxychloride → HCID 10377394, compound
Reaction equation
[C:1]([C:5]1[C:14](=O)[C:13]2[C:8](=[C:9]([O:16][CH3:17])[CH:10]=[CH:11][CH:12]=2)[NH:7][CH:6]=1)(=[O:4])[CH2:2][CH3:3].P(Cl)(Cl)([Cl:20])=O>>[C:1]([C:5]1[CH:6]=[N:7][C:8]2[C:13]([C:14]=1[Cl:20])=[CH:12][CH:11]=[CH:10][C:9]=2[O:16][CH3:17])(=[O:4])[CH2:2][CH3:3]Participants
3
Procedure
3-Propanoyl-8-methoxy-4(1H)-quinolone (35.4 g, 0.15 mol) was dissolved in phosphoryl chloride (400 ml) and heated at reflux for 1 hour, then the excess phosphoryl chloride evaporated. The residue was mixed with ice, then diluted with water and extracted into dichloromethane. Drying and evaporation gave 3-propanoyl-4-chloro-8-methoxyquinoline (39.7 g) as a dark oil which was used without further purification.
Workup
- temperatureheated
- temperatureat reflux for 1 hour
- customthe excess phosphoryl chloride evaporated
- additionThe residue was mixed with ice
- additiondiluted with water
- extractionextracted into dichloromethane