Ammonia → (5-Chloro-2-(1H-1,2,4-triazol-1-YL)phenyl)methanamine

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To a suspension of 5-Chloro-2-[1,2,4]triazol-1-yl-benzonitrile (11.87 g, 58 mmol) in EtOH saturated with NH3 (500 ml) was added Raney Nickel (ca. 5 pipets of suspension in water, washed/decanted with EtOH several times). The mixture was hydrogenated at 1 atm for 26 h. The reaction mixture was filtered on celite under a flow of argon and the filtrate was concentrated in vacuo. The crude product was purified by flash chromatography (silica gel, 5% MeOH containing 10% NH4OH in CH2Cl2 to 10%) to give 5-Chloro-2-[1,2,4]triazol-1-yl-benzylamine as a white solid. 1H NMR (CDCl3, 400 MHz) δ 8.47 (s, 1H); 8.14 (s, 1H); 7.58 (d, J=2.3 Hz, 1 H); 7.38 (dd, J=2.3, 7.9 Hz, 1 H); 7.30 (d, J=7.9 Hz, 1 H); 3.70 (s, 2 H). 8.72 (d, J=4.8 Hz, 1 H); 8.42 (s, 1H); 8.18 (s, 1H); 7.70 (d, J=7.6 Hz, 1 H); 7.40 (dd, J=4.8, 7.6 Hz, 1 H); 5.85 (bs, 1 H); 4.43 (d, J=5.4 Hz, 2 H); 1.45 (s, 9 H).

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