N1-Phenyl-4-(trifluoroMethyl)benzene-1,2-diaMine synthesis

7synthesis methods

Product Name:N1-Phenyl-4-(trifluoroMethyl)benzene-1,2-diaMine
CAS Number:1651-43-0
Molecular formula:C13H11F3N2
Molecular Weight:252.24

Benzenamine, 2-nitro-N-phenyl-4-(trifluoromethyl)-

2715-01-7
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N1-Phenyl-4-(trifluoroMethyl)benzene-1,2-diaMine

1651-43-0
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Yield:1651-43-0 99%

Reaction Conditions:

with iron;ammonium chloride in ethanol;water; for 6 h;Reflux;

Steps:

2-Amino-N-phenyl-4-(trifluoromethyl)aniline (2)

Iron powder (1.04 g, 18.6 mmol, 4.79 equiv.) and saturated aqueous NH₄Cl (5 mL) were added to a mixture of nitroaniline 1 (1.082 g, 3.88 mmol) in 25 mL of ethanol. The mixture was refluxed for 6 hours. The darkened mixture was cooled to room temperature, filtered through celite, and extracted twice with DCM. The organic layers were combined, washed twice with water, and concentrated at in vacuo. The reddish residue solidified and yielded the desired product 2 (0.967 mg, 3.83 mmol, 99%).¹HNMR (400 MHz, CDCl₃): δ = 3.89 - 3.42 (broad s, 2H), 5.32 (s, 1H),6.87 (d, J = 7.8 Hz, 2H), 6.94 (t, J = 7.4 Hz, 1H), 7.01 (d, J= 9.8 Hz, 2H), 7.19 (d, J = 8.0 Hz, 1H), 7.30 - 7.24 (m, 2H). ¹³CNMR (101 MHz, CDCl₃): δ = 112.97, 113.01, 116.34, 116.38, 117.04,120.91, 121.07, 122.98, 125.68, 125.73, 126.05, 128.88, 129.45, 133.07, 139.66,143.30 ppm. ¹⁹F NMR (376 MHz, CDCl₃) δ -61.88. HR-MS (ESI) m/z: calcd. for [C₁₃H₁₁F₃N₂+ H]⁺: 253.0952; found: 253.0932.