81764-16-1

23833-99-0

81764-16-1

GENERAL METHOD: 4-Chloro-8-nitroquinoline (90 mg, 0.292 mmol) was dissolved in ethanol (2 mL) and iron powder (163 mg, 2.92 mmol) and ammonium chloride (127 mg, 2.33 mmol) were added sequentially. The reaction mixture was heated and refluxed for 2 hours. Upon completion of the reaction, the reaction mixture was filtered through diatomaceous earth and the diatomaceous earth bed was washed with a chloroform solution of 10% methanol. The filtrate was washed sequentially with saturated aqueous sodium bicarbonate solution and pure water. The organic layer was separated, dried over anhydrous sodium sulfate and filtered, and concentrated to give 70 mg of the target product 4-chloro-8-aminoquinoline. The product was confirmed by 1H NMR (300 MHz, DMSO-d6) and mass spectrometry (MS). Synthesis of 4-chloro-8-aminoquinoline: 200 mg of the target product was obtained by reaction using a mixed solution of ethanol (6 mL) and water (3 mL) of 4-chloro-8-nitroquinoline (250 mg, 1.20 mmol), ammonium chloride (513 mg, 9.60 mmol), and iron powder (671 mg, 12.0 mmol) according to the above general method. The product was confirmed by 1H NMR (400 MHz, CDCl3) and mass spectrometry (MS).