Cl.Cl[CH2:3][C:4]1[CH:13]=[CH:12][C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=1.[OH:14][C:15]1[CH:20]=[CH:19][C:18]([CH2:21][C:22]([O:24][CH3:25])=[O:23])=[CH:17][CH:16]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[N:5]1[C:6]2[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=2)[CH:12]=[CH:13][C:4]=1[CH2:3][O:14][C:15]1[CH:16]=[CH:17][C:18]([CH2:21][C:22]([O:24][CH3:25])=[O:23])=[CH:19][CH:20]=1To a mixture of 2-(chloromethyl)quinoline hydrochloride (1 g, 4.6 mmol) and methyl p-hydroxyphenylacetate (0.83 g, 5 mmol) in anhydrous dimethylformamide (20 mL), was added potassium carbonate (2.33 g) and the mixture was heated at 60° C. for 8 h. Dimethylformamide was removed, and the residue was partitioned between water and chloroform. The organic phase was dried over sodium sulfate and the solvent was removed, to afford 1.68 g of a crude product that was purified by chromatography on silica gel (ethyl acetatehexane 1:1), to give 1.2 g of the title compound (yield: 84%).
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