1-[4-(2-Aminoanilino)phenyl]-2,2,2-trifluoroethanone

In the title compound, C14H11F3N2O, the two aromatic rings are oriented at a dihedral angle of 70.84 (8)°. The crystal structure displays intermolecular N—H⋯O and N—H⋯F interactions.

In the title compound, C 14 H 11 F 3 N 2 O, the two aromatic rings are oriented at a dihedral angle of 70.84 (8) . The crystal structure displays intermolecular N-HÁ Á ÁO and N-HÁ Á ÁF interactions.  Table 1 Hydrogen-bond geometry (Å , ). Comment 2,2,2-Trifluoroacetophenones are well known as building-blocks in the synthesis of therapeutic agents for example as acetylcholinesterase inhibitors (Colard et al., 1994), as anticonvulsants (Schenck et al., 2004) or as hPPAR agonists. The title compound was prepared in the course of our studies on acetophenone derivatives as potent p38 mitogen-activated protein (MAP) kinase inhibitors.

Experimental
For the preparation of the title compound a mixture of 501 mg (2.4 mmol) 1-(4-chlorophenyl)-2,2,2-trifluoroethanone, 332 mg (2.4 mmol) 2-nitroaniline, 1400 mg (4.3 mmol) Cs 2 CO 3 ,90 mg (0.19 mmol) 2-(dicyclohexylphosphino)-2'-, 4'-, 6'-triisopropylbiphenyl and 20 mg (0.09 mmol) Pd(OAc) 2 in 2 ml absolute tert-butanol and 8 ml absolute toluol was stirred for 2 h at 90 °C under an atmosphere of argon. The mixture was diluted with water then extracted with ethyl acetate. The extracts were combined, washed with saturated saline solution, and then dried over Na 2 SO 4 . The solvent was removed under vacuum and the crude product was dissolved in 10 ml ethanol, 840 mg (3.71 mmol) tin(II)chloride-dihydrate was added and stirred for 5 h at 348 K. After cooling down to room temperature the mixture was quenched with 20 ml ice-water and after alkalization with NaOH (20 %) extracted three-times with ethyl acetate. The combined organic layer was washed twice with water, dried (Na 2 SO 4 ), and evaporated under reduced pressure. The residue was purified by flashchromatography (SiO 2 60, hexane / ethyl acetate) (yield: 21.5 %). Crystals of the title compound were obtained by slow evaporation of a methanol d6solution at room temperature.

Refinement
Hydrogen atoms attached to carbons were placed at calculated positions with C-H = 0.95 Å (aromatic) or 0.98-0.99 Å (sp 3 C-atom). Hydrogen atoms attached to N7 and N8 were located in difference Fourier maps. All H atoms were refined in the riding-model approximation with isotropic displacement parameters set at 1.2-1.5 times of the U eq of the parent atom.

Special details
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.
Refinement. Refinement of F 2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F 2 , conventional R-factors R are based on F, with F set to zero for negative F 2 . The threshold expression of F 2 > σ(F 2 ) is used only for calculating Rfactors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F 2 are statistically about twice as large as those based on F, and R-factors based on ALL data will be even larger.