Ammonium Chloride → HCID 58154634, compound

Participants

Reaction Conditions

Reaction Steps

Crude 2-(3-fluoro-5-(trifluoromethyl)phenyl)-8-nitroquinoline (2.78 mmol) was taken up in isopropyl alcohol (120 mL) and ammonium chloride (150 mg, 2.8 mmol) in water (20 mL) was added. The mixture was heated to 90° C., iron powder (550 mg, 9.85 mmol) was added and the reaction was continued stirring at 90° C. 18 hours. The reaction mixture was filtered over celite and the celite cake was washed with ethyl acetate (150 mL). The filtrate was concentrated and the residue was taken up in 1N aqueous NaOH (80 mL) and extracted with ethyl acetate (3×25 mL). The organic layers were combined, washed with brine, dried (MgSO4), and concentrated. The crude material was purified by flash chromatography (a gradient of 0 to 100% ethyl acetate in pentane) to obtain 2-(3-fluoro-5-(trifluoromethyl)phenyl)quinolin-8-amine (0.42 g, 1.37 mmol, 49% yield over two steps).

Provenance & Evidence