[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]=[C:8](Cl)[CH:7]=[C:6]2[CH3:14].[CH3:15][OH:16].C[O-].[Na+]>O>[CH3:15][O:16][C:8]1[CH:7]=[C:6]([CH3:14])[C:5]2[C:10](=[CH:11][CH:12]=[C:3]([O:2][CH3:1])[CH:4]=2)[N:9]=1A 1-liter, four-necked round bottom flask equipped with a mechanical stirrer, condenser, thermowatch and addition funnel was charged with 6-methoxy-4-methyl-2-chloroquinoline (3) (20.75 g, 0.1 moles) and methanol (250 ml). Methanolic sodium methoxide (25%, 108 g, 0.5 moles) was added over 15 minutes. The resulting mixture was heated to reflux and held for 24 hours. Additional methanolic sodium methoxide was added (25%, 42 g, 0.2 moles) and the reaction was refluxed an additional 21 hours. The mixture was cooled to 60° C. and water (200 ml) was added slowly. The slurry was cooled to 10° C., the product isolated by suction filtration, washed with water, and air dried. Yield was 17.9 g (88.2%); mp=58-59° C.; purity by HPLC=100 area %.
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