Phosphorus oxychloride → 3-Isobutyryl-4-chloro-8-methoxyquinoline
Reaction equation
[C:1]([C:6]1[C:15](=O)[C:14]2[C:9](=[C:10]([O:17][CH3:18])[CH:11]=[CH:12][CH:13]=2)[NH:8][CH:7]=1)(=[O:5])[CH:2]([CH3:4])[CH3:3].P(Cl)(Cl)([Cl:21])=O>C(Cl)(Cl)Cl>[Cl:21][C:15]1[C:14]2[C:9](=[C:10]([O:17][CH3:18])[CH:11]=[CH:12][CH:13]=2)[N:8]=[CH:7][C:6]=1[C:1](=[O:5])[CH:2]([CH3:4])[CH3:3]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
3-Isobutyryl-8-methoxy-4(1H)-quinolone (8.31 g, 0.034 mol) was heated under reflux in a mixture of phosphorus oxychloride (20 ml) and chloroform (30 ml) for 30 minutes. The mixture was evaporated and the residue was partitioned between dichloromethane and sodium hydrogen carbonate solution. The organic solution was washed with sodium hydrogen carbonate solution, water and brine, dried, filtered and evaporated to give 4-chloro-3-isobutyryl-8-methoxyquinoline as a brown oil (6.4 g, 71%).