[NH2:1][C:2]1[C:7](=[O:8])[N:6]([CH2:9][C:10]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][C:11]=2[O:18][CH3:19])[CH2:5][CH2:4][C:3]=1[C:20]([O:22][CH2:23][CH3:24])=[O:21].ClC1C(=O)C(C#N)=C(C#N)C(=O)C=1Cl>C1(C)C=CC=CC=1.C(OCC)(=O)C>[NH2:1][C:2]1[C:7](=[O:8])[N:6]([CH2:9][C:10]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][C:11]=2[O:18][CH3:19])[CH:5]=[CH:4][C:3]=1[C:20]([O:22][CH2:23][CH3:24])=[O:21]To a solution of ethyl 5-amino-1-(2,4-dimethoxybenzyl)-6-oxo-1,2,3,6-tetrahydropyridine-4-carboxylate (890 mg) in toluene (20 ml) was added 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (785 mg) at room temperature, and the mixture was heated under reflux for 30 min, allowed to be cooled to room temperature, and diluted with ethyl acetate. The insoluble material was filtered, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (535 mg).
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