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

Participants

Reaction Steps

To a 250 mL round-bottomed flask was added 3-azidomethyl-7-chloro-1-phenyl-1H-quinolin-4-one (2.00 g, 6.44 mmol), ethyl acetate (120 mL) followed by platinum (IV) oxide (152 mg, 0.671 mmol). The reaction mixture was evacuated and back-filled with hydrogen gas using an atmospheric hydrogenation apparatus. The reaction mixture was stirred under hydrogen gas (1 atm.) at room temperature for 5 hr. TLC (40% ethyl acetate-hexanes) and LCMS indicated the absence of starting material. The reaction mixture was filtered through celite under N2 atmosphere, then the celite layer was washed with ethyl acetate. The combined filtrate and washings were concentrated to give 3-aminomethyl-7-chloro-1-phenyl-1H-quinolin-4-one (1.77 g, 96.6% crude yield) as a light beige/greyish solid. The material was used in the next step without further purification.

Provenance & Evidence