[Cl-].[Al+3].[Cl-].[Cl-].[N:5]1([C:15]([O:17][CH2:18][CH3:19])=[O:16])[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH2:8][CH2:7][CH2:6]1.[Cl:20][CH2:21][CH2:22][C:23](Cl)=[O:24].O>ClCCl>[Cl:20][CH2:21][CH2:22][C:23]([C:11]1[CH:10]=[C:9]2[C:14](=[CH:13][CH:12]=1)[N:5]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH2:6][CH2:7][CH2:8]2)=[O:24]Aluminum chloride (23.5 g, 176 mmol) was added to a solution of ethyl 3,4-dihydro-1(2H)-quinoline carboxylate (14.5 g, 70.4 mmol) and 3-chloropropionyl chloride (7.39 ml, 77.4 mmol) in dichloromethane under cooling with water-bath, and the mixture was stirred at room temperature for 14 hours. The reaction solution was poured into iced water and extracted with dichloromethane. The extract was washed with a saturated saline solution and dried over anhydrous sodium sulfate, and the solvent was distilled away under reduced pressure. The resulting residues were purified by silica gel column chromatography (developing solvent; hexane:ethyl acetate=3:1) and crystallized from hexane, whereby the title compound (15.6 g) was obtained as colorless powder with a mp. of 78 to 79° C.
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