[CH3:1][N:2]1[C:11]2[CH2:10][CH:9]([C:12]3[CH:16]=[CH:15][S:14][CH:13]=3)[CH2:8][C:7](=O)[C:6]=2[C:5]([CH3:18])=[CH:4][C:3]1=[O:19].[C:20]([NH:23][NH2:24])([NH2:22])=[NH:21].[ClH:25].Cl>C(O)C>[ClH:25].[CH3:1][N:2]1[C:11]2[CH2:10][CH:9]([C:12]3[CH:16]=[CH:15][S:14][CH:13]=3)[CH2:8][C:7](=[N:24][NH:23][C:20]([NH2:22])=[NH:21])[C:6]=2[C:5]([CH3:18])=[CH:4][C:3]1=[O:19]To a mixture of 1,4-dimethyl-7-(thiophen-3-yl)-1,2,5,6,7,8-hexahydroquinoline-2,5-dione (0.1 g) and aminoguanidine hydrochloride (41 mg) were added ethanol (3 ml) and 2N hydrochloric acid (0.2 ml), and the mixture was refluxed for 4 hours and concentrated under reduced pressure. To the residue was added ethanol (1 ml), and precipitated crystals were filtered, washed with ethanol and dried to give 1,4-dimethyl-5-guanidinoimino-7-(thiophen-3-yl)-1,2,5,6,7,8-hexahydroquinolin-2-one hydrochloride (Compound 137) (0.125 g) as colorless crystals.
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