Sodium Hydroxide → 4-Trifluoroacetylaniline

To a suspension of 2,2,2-trifluoro-1-(4-nitro-phenyl)-ethanone (4.5 g, 20.5 mmol) in concentrated hydrochloric acid (15 ml) and water (15 ml) was added tin (II) chloride (14 g, 74 mmol). After stirring for 24 hours, the mixture was adjusted to pH 10 by addition of aqueous sodium hydroxide solution (50%) and extracted with ethyl acetate. The organic extract was concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel eluting with ethyl acetate-hexane (1:5) followed by recrystallization (ethyl acetate-hexane) to afford 1-(4-amino-phenyl)-2,2,2-trifluoro-ethanone (750 mg, 19% yield).