Hydrochloric Acid → 7-(2-Bromothiophen-3-yl)-5-(1-hydroxyguanidin-3-yl)imino-4-methyl-5,6,7,8-tetrahydroquinoline hydrochloride

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Reaction Conditions

Reaction Steps

To a mixture of 7-(2-bromothiophen-3-yl)-4-methyl-5,6,7,8-tetrahydroquinolin-5-one (0.245 g) and 1-amino-3-hydroxyguanidine p-toluenesulfonate (262 mg) were added ethanol (3 ml) and concentrated hydrochloric acid (0.1 ml), and the mixture was stirred at 90° C. for 2 hours. Under reduced pressure, the solvent was evaporated, and to the residue was added 0.2N sodium hydroxide solution (20 ml). The mixture was extracted with a mixture of ethyl acetate (20 ml) and tetrahydrofuran (20 ml). The organic layer was washed with 0.2N sodium hydroxide solution (20 ml) and water, to which was added 2N hydrochloric acid (0.8 ml). The mixture was concentrated, and to the residue was added ethanol (3 ml). The mixture was stirred at 90° C. for 3 hours and cooled, and precipitated crystals were filtered, washed with ethanol and dried to give 7-(2-bromothiophen-3-yl)-5-(1-hydroxyguanidin-3-yl)imino-4-methyl-5,6,7,8-tetrahydroquinoline hydrochloride (Compound 125) (0.215 g) as pale yellow crystals.

Provenance & Evidence