[NH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH2:4][CH2:3][CH2:2]1.[H-].[Na+].BrC[CH2:20][C:21]1[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][CH:22]=1.O>CN(C=O)C.C(OCC)(=O)C>[Cl:27][C:24]1[CH:25]=[CH:26][C:21]([CH2:20][N:1]2[C:10]3[C:5](=[CH:6][CH:7]=[CH:8][C:9]=3[C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH2:4][CH2:3][CH2:2]2)=[CH:22][CH:23]=1To a mixture of ethyl 1,2,3,4-tetrahydroquinoline-8-carboxylate (1.1 g) and DMF (9.0 mL) was added sodium hydride (55% dispersion in paraffin liquid, 280 mg) at 0° C., followed by stirring at room temperature for 30 minutes. To the reaction mixture was added a solution of 1-(bromoethyl)-4-chlorobenzene (1.2 g) in DMF (2.0 mL) under ice-cooling, followed by stirring at room temperature for 3 days. To the reaction mixture was added sodium hydride (55% dispersion in paraffin liquid, 280 mg), followed by stirring for 1 day. To the reaction mixture were added water and ethyl acetate, and a liquid-separation operation was carried out. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. After filtration, the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane-ethyl acetate) to obtain ethyl 1-(4-chlorobenzyl)-1,2,3,4-tetrahydroquinoline-8-carboxylate (510 mg).
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