3-Amino-4-(trifluoromethyl)benzonitrile

Preparation of 3-amino-4-(trifluoromethyl)benzonitrile [00163] A solution of 3-(4-methoxybenzylamino)-4-(trifluoromethyl)benzonitrile (500 mg, 1.63 mmol) and triethylsilane (0.2 mL) in dichloroethane (2 mL) was treated with TFA (1 mL) and stirred at room temperature for 30 min. The reaction mixture was concentrated to obtain Intermediate 24 (284 mg, 93 percent yield) as an orange solid. HPLC: Rt = 1.24 min. (PHENOMENEX.(R). S5 4.6 x 30 mm, 10-90percent aqueous methanol containing 0.1percent TFA(a) 3-lsothiocvanato-4-trifluoromethyl-benzonitrileA mixture of (a) 3-Isothiocyanato-4-trifluoromethyl-benzonitrile A mixture of (a) 3-Amino-4-trifluoromethyl-benzonitrileA closed pressure tube charged with 3-fluoro-4-trifluoromethyl-benzonitrile (10.0 g; 52.9 mmol) and liquid NH3 (60 mL) was heated for 6 days at 90 C. The tube was cooled to -60 C and opened. The mixture was allowed to stir for 1 h at rt, washed with brine, extracted with EtOAc, dried over Na2S04, filtered and concentrated..Yield: 10.2 g (quantitative; slightly contaminated).(a) 3-Amino-4-(trifluoromethyl)benzonitrileA closed pressure tube charged with 3-fluoro-4-(trifluoromethyl)benzonitrile (10.0 g; 52.9 mmol) and liquid NH3 (60 ml.) was heated for 6 days at 9O0C. The tube was cooled to - 600C and opened. The mixture was allowed to stir for 1 h at rt. The residue was treated with brine and extracted with EtOAc to give the crude sub-title compound (10.2 g).(a) 3-Amino-4-trifluoromethyl-benzonitrile A closed pressure tube charged with 3-fluoro-4-trifluoromethyl-benzonitrile (10.0 g; 52.9 mmol) and liquid NH3 (60 mL) was heated for 6 days at 90 C. The tube was cooled to -60 C. and opened. The mixture was allowed to stir for 1 h at rt, washed with brine, extracted with EtOAc, dried over Na2SO4, filtered and concentrated. Yield: 10.2 g (quantitative; slightly contaminated).(b) tert-Butyl 5-cyano-2-trifluoromethyl-phenylcarbamateA mixture of (b) tert-Butyl 5-cyano-2-trifluoromethyl-phenylcarbamate A mixture of (b) tert-Butyl N-[5-cyano-2-(trifluoromethyl)phenyl1-carbamateA mixture of Preparation of

Molecular Weight:186.13
XLogP3:1.8
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:5
Exact Mass:186.04048265
Monoisotopic Mass:186.04048265
Topological Polar Surface Area:49.8
Heavy Atom Count:13
Complexity:227
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes