3-azidomethyl-7-chloro-1-(2-chloro-phenyl)-1H-quinolin-4-one → 3-aminomethyl-7-chloro-1-(2-chloro-phenyl)-1H-quinolin-4-one

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Reaction Steps

To a 100 mL round-bottom flask was added 3-azidomethyl-7-chloro-1-(2-chloro-phenyl)-1H-quinolin-4-one (215 mg, 0.623 mmol), ethyl acetate (20 mL) followed by platinum (IV) oxide (18.0 mg, 0.079 mmol). The reaction vessel was evacuated and back-filled with hydrogen gas via a balloon. Almost immediately the reddish color of the PtO2 turned black. The reaction mixture was stirred under a balloon of hydrogen gas at room temp overnight. The reaction mixture was filtered through a bed of celite. The filtrate was concentrated to give the crude 3-aminomethyl-7-chloro-1-(2-chloro-phenyl)-1H-quinolin-4-one (152 mg, 76.4%, 81% purity by HPLC). 1H NMR (DMSO-d6) δ ppm 8.23 (d, J=8.7 Hz, 1H) 7.80-7.92 (m, 2H) 7.59-7.79 (m, 3H) 7.41 (dd, J=8.7, 1.8 Hz, 1H) 6.66 (d, J=1.8 Hz, 1H) 3.58 (s, 2H) 1.69 (br. s., 2H). MS calcd. for C16H12Cl2N2O [(M+H)+] 320.0, obsd. 318.9, [(M-NH2)+] 303.0, obsd. 301.9.

Provenance & Evidence