3-(Trifluoromethyl)aniline → STK345463

Participants

Reaction Steps

2-Chloropyridine-3-carbonyl chloride (18.02 g, 0.102 mol) in CH2Cl2 (100 ml) was added dropwise (via an addition funnel) to a stirred solution of 3-(trifluoromethyl)-aniline (15.00 g, 0.093 mol) and DIEA (24.39 ml, 0.14 mol) in CH2Cl2 (500 ml) at 0° C. The mixture gradually was warmed to RT. The reaction continued for 18 h before washing several times with saturated NaHCO3 aqueous solution and brine, respectively. The organic layer was dried over Na2SO4 and evaporated. The resulting oil was purified over silica gel with EtOAc/hexane (2:1) as eluant to leave the amide as a white solid (26.08 g). MS: (ES+) 301 (M+1)+; (ES−): 299 (M−1)−. Calc'd for C13H8ClF3N2O: 300.03.

Provenance & Evidence