1337523-99-5

66361-67-9

1337523-99-5

6-Bromo-3,4-dihydronaphthalen-1(2H)-one (9.5 g, 42.2 mmol) was used as raw material and suspended in 2-propanol (250 mL). Subsequently, sodium cyanoborohydride (NaBH3CN, 13.3 g, 211 mmol) and ammonium acetate (65.1 g, 844 mmol) were added sequentially. The reaction mixture was stirred at room temperature for 4 hours before heating to reflux and continuing to stir for 22 hours. Upon completion of the reaction, the mixture was cooled to room temperature, poured into ice water (500 mL) and the pH was adjusted with sodium hydroxide solution to >10. The mixture was extracted with dichloromethane (CH2Cl2, 2 x 25 mL), the organic layers were combined and dried with anhydrous magnesium sulfate (MgSO4). After filtration, the crude product (9.842 g) was obtained by vacuum concentration. Purification by fast chromatography (silica gel, 100 g, eluent 2% to 10% dichloromethane solution in methanol) afforded the target compound 6-bromo-1,2,3,4-tetrahydronaphthalen-1-amine (8.08 g, 85% yield) as a light red oil. The mass spectrum (MS) showed [M+H]+ m/z 226.0 (with IBr isotope).