Water → 3-Chloro-5-fluoro-4-(quinolin-3-yloxy)phenylamine

Participants

Reaction Steps

To a solution of 3-Chloro-5-fluoro-4-(quinolin-3-yloxy)nitrobenzene (186.1) (0.980 g) and NH4Cl (1.64 g) in EtOH(50 ml)-H2O (5 ml), was added iron powder (1.92 g). The mixture was heated to reflux for 1 hr. After cooling the reaction mixture was filtered through short celite pad. The filtrate was concentrated, diluted with sat. NaHCO3 and extacted with AcOEt(30 ml×3). The combined organic layeres were washed with brine and dried over Na2SO4. Concentration of solvent afford crude product, which was purified by column chromatography (silicagel, AcOEt:Hexane=1:3) to provide aniline 186.2 (0.420 g) as a colorless solid.

Provenance & Evidence