Phosphorus oxychloride → 2-Chloro-6,7-dimethylquinoline-3-carbonitrile
Reaction equation
[C:1]([C:3]1[C:4](=O)[NH:5][C:6]2[C:11]([CH:12]=1)=[CH:10][C:9]([CH3:13])=[C:8]([CH3:14])[CH:7]=2)#[N:2].P(Cl)(Cl)([Cl:18])=O>>[Cl:18][C:4]1[C:3]([C:1]#[N:2])=[CH:12][C:11]2[C:6](=[CH:7][C:8]([CH3:14])=[C:9]([CH3:13])[CH:10]=2)[N:5]=1Participants
3
Procedure
A mixture was prepared from 67.5 g of 3-cyano-6,7-dimethyl-2(1H)-quinolinone and 340 ml of phosphoryl chloride and this was heated at reflux for 18 hours. The mixture was cooled, excess phosphoryl chloride was removed by vacuum evaporation, and the residue was carefully added to water with vigorous stirring. The solid which formed was separated by filtration and recrystallized from methylene chloride to give 2-chloro-3-cyano-6,7-dimethylquinoline melting at about 189°-190° C.
Workup
- temperaturethis was heated
- temperatureat reflux for 18 hours
- temperatureThe mixture was cooled