3-(Trifluoromethyl)aniline → STK345463

Participants

Reaction Steps

A solution of 3-aminobenzotrifluoride (Ruka, Buchs, Switzerland; 2.5 mL, 2.90 g, 18 mmol) in ethyl acetate (40 mL) is added to a stirred aqueous solution of sodium hydroxide (40 mL of 1 M, at room temperature. This stirred solution is then treated dropwise over 30 minutes with a solution of 2-chloronicotinoyl chloride (Lancaster Synthesis, Lancashire, England; 3.52 g, 20 mmol) in dry ethyl acetate (25 mL). The resulting mixture is then stirred for 2 h at ambient temperature. The mixture is then extracted with ethyl acetate (3×100 mL) and the combined extracts are sequentially washed with water (2×100 mL), hydrochloric acid (2×100 mL of 2M), water (2×100 mL), saturated aqueous sodium hydrogen carbonate solution (2×100 mL) and saturated aqueous sodium chloride (1×100 mL), dried (Na2SO4), filtered and the solvent is evaporated off under reduced pressure to yield the crude product which is purified by recrystallisation from ethyl acetate-hexane to give the title compound as a colourless crystalline solid, m.p. 117-118° C.

Provenance & Evidence