3-(Trifluoromethyl)aniline → STK345463

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.

1. customat room temperature
2. extractionThe mixture is then extracted with ethyl acetate (3×100 mL)
3. washthe 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)
4. dry with materialdried (Na2SO4)
5. filtrationfiltered
6. customthe solvent is evaporated off under reduced pressure
7. customto yield the crude product which
8. customis purified by recrystallisation from ethyl acetate-hexane

ORD record

ord-a6d4c913a5814d7e8e784443fbdd278d

Source dataset

uspto-grants-2003_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06624174B2