3,4-difluoro-N-(2-nitrophenyl)aniline → N-(3,4-difluorophenyl)benzene-1,2-diamine

Participants

Reaction Steps

A solution of 3,4-difluoro-N-(2-nitrophenyl)aniline (22.76 g, 91 mmol) in 50% ethyl acetate/methanol (500 mL) was treat with palladium on carbon 10 w. % loading, matrix activated carbon support (3.07 g). The reaction mixture was placed on the Parr shaker for 3 h at 60 psi. The reaction mixture was filtered through celite and evaporated. The crude reaction product was purified by flash chromatography (SiO2, 3→50% ethyl acetate/heptane) to provided N-(3,4-difluorophenyl)benzene-1,2-diamine (10.17 g, 51%) as a brown solid: HPLC purity 99.9% at 210-370 nm, 9.4 min.; Xterra RP18, 3.5 u, 150×4.6 mm column, 1.2 mL/min, 85/15-5/95 (Ammon. Form. Buff. Ph=3.5/ACN+MeOH) for 10 min, hold 4 min.

Provenance & Evidence