[CH3:1][C:2]1[NH:3][C:4]2[C:9]([C:10](=O)[CH:11]=1)=[CH:8][C:7]([CH3:13])=[CH:6][CH:5]=2.[OH-].[Na+].C([O-])([O-])=O.[Na+].[Na+].P(Cl)(Cl)([Cl:24])=O>>[Cl:24][C:10]1[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([CH3:13])[CH:8]=2)[N:3]=[C:2]([CH3:1])[CH:11]=1A mixture of 2,6-dimethyl-1H-quinolin-4-one (17.3 g, 100 mmol) and phosphorus oxychloride (30 mL) was heated at 80° C. for 3 h. After cooling down to room temperature, the reaction mixture was poured onto ice. The resulting solution was carefully alkalinized to pH 8–9 with 0.5 N NaOH and saturated Na2CO3. The solution was extracted with CH2Cl2 (200 mL×3). The organic layer was separated, dried over magnesium sulfate, and concentrated under reduced pressure. The crude product was purified by column chromatography (10% ethyl acetate in n-hexane) to give 4-chloro-2,6-dimethyl-quinoline (12.4 g, 65% yield).
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