ChemicalBook CAS DataBase List 5-Trifluoromethyl-pyridin-3-ylamine

5-Trifluoromethyl-pyridin-3-ylamine synthesis

5synthesis methods

Product Name:5-Trifluoromethyl-pyridin-3-ylamine
CAS Number:112110-07-3
Molecular formula:C6H5F3N2
Molecular Weight:162.11

2-CHLORO-3-NITRO-5-(TRIFLUOROMETHYL)PYRIDINE

72587-15-6

112110-07-3

Step Ia: 5-(Trifluoromethyl)-2-chloro-3-nitropyridine (0.850 g, 3.75 mmol) was dissolved in methanol (17 mL), and palladium carbon (800 mg, 10% wetted, 0.375 mmol) was added. The reaction mixture was hydrogenated for 16 h at 60 psi hydrogen pressure and 20 °C. The progress of the reaction was monitored by LCMS to confirm that the starting material (M + H 213/215, 3:1) and hydroxylamine intermediate were completely consumed and a mixture of partially reduced product (M + H 163; UVmax 214, 258, 332 nm) and completely reduced product (M + H 169; no UV absorption) was detected. After completion of the reaction, the reaction mixture was filtered and the filter cake was washed well with methanol. The filtrate was concentrated in vacuum to give 0.74 g of product in the form of HCl salt. Subsequently, the product was purified by preparative HPLC/MS using a 30 mm × 100 mm C18 column; the mobile phase was 20% acetonitrile-water (containing 0.1% NH4OH), with an initial hold of 1 min and a gradient up to 40% over 6 min; the flow rate was 60 mL/min; the detector was set at m/z 163; and the product retention time was 4.4 min. Fractions containing the pure product were collected, combined and concentrated to give 52 mg of the product as an oil in 8% yield.1H NMR (CDCl3) δ 8.26 (s, 1H); 8.24 (d, 1H); 7.15 (t, 1H); 4.00 (s, 2H).

3-Pyridinamine, N-(diphenylmethylene)-5-(trifluoromethyl)-

1529769-93-4
0 suppliers
inquiry

112110-07-3
147 suppliers
$19.00/250mg

Yield: 90%

Reaction Conditions:

with hydrogenchloride in tetrahydrofuran;water at 20; for 2 h;

Steps:

2 Step 2: Synthesis of 5-(trifluoromethyl)pyridin-3-amine
Dissolve the imine obtained in Step 1 (850 mg, 2.6 mmol) in THF (10 mL), add water (2 mL), IN HCI solution (5 mL), stir the reaction at room temperature for 2 hrs. After the reaction, extract with EtOAc, wash the organic layer with saturated NaHC0₃ solution and brine sequentially, dry over anhydrous Na₂S0₄, and concentrate under reduced pressure to give the crude product. Purification by chromatography (silica gel, EtOAc:PE=l :l) affords the target compound (380 mg, 90%).

References:

CROWN BIOSCIENCE INC. (TAICANG);ZHANG, Deyi;ZHANG, Ruihao;ZHONG, Boyu;SHIH, Chuan WO2014/418, 2014, A1 Location in patent:Page/Page column 83

85148-26-1 Synthesis