2-Fluoro-6-methoxybenzylamine

Synthesis

94088-46-7

150517-75-2

General procedure for the synthesis of 2-fluoro-6-methoxybenzylamine from 2-fluoro-6-methoxybenzonitrile: 30 g of Raney nickel catalyst was added to a 1.0 L methanol solution containing 2-fluoro-6-methoxybenzonitrile (228 g, crude) and 145 mL ammonium hydroxide. The reaction mixture was transferred to an autoclave and stirred at 40 °C and 25 atm hydrogen atmosphere for 8 hours. Upon completion of the reaction, the catalyst was removed by filtration and the filtrate was concentrated under reduced pressure to give a light yellow oil. The oily material was further purified by decompression distillation to give 2-fluoro-6-methoxybenzylamine (60 g, 54% yield) as a colorless oil. The product was characterized by 1H NMR (500 MHz, DMSO-d6): δ 1.58 (s, 2H), 3.67 (s, 1H), 6.75 (t, 1H), 6.82 (d, 1H), 7.22 (dd, 1H).LC-MS analysis showed [MH]+ = 156.1.

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