[CH3:1][O:2][C:3](=[O:11])[C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[N:6][CH:5]=1.C([O-])([O-])=O.[K+].[K+].Cl.Cl[CH2:20][C:21]1[CH:30]=[CH:29][C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[N:22]=1>CN(C=O)C>[CH3:1][O:2][C:3](=[O:11])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:20][C:21]2[CH:30]=[CH:29][C:28]3[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=3)[N:22]=2)=[N:6][CH:5]=1To a solution of 6-hydroxynicotinic acid methyl ester (10.0g, 0.0652 mol), prepared as in step 1, in DMF (350 ml) at room temperature was added anhydrous K2CO3 (19.0 g, 0.137 mol) followed by 2-chloromethylquinoline hydrochloride (14.0 g, 0.0652 mol), and the mixture was allowed to stir at room temperature overnight. Once the starting material was consumed, water (700 ml) was added to the mixture, and the aqueous layer was extracted with ethyl acetate. The organic layer was washed with brine, dried over MgSO4, and concentrated in vacuo. The resulting white precipitate was filtered and washed with hexanes to give 15.20 g of 6-(quinol-2-ylmethoxy)nicotinic acid methyl ester.
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