116548-04-0 | Pyridine-derivatives

Electric Literature of 116548-04-0, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 116548-04-0, name is 2-Oxo-6-(trifluoromethyl)-1,2-dihydropyridine-3-carbonitrile, molecular formula is C7H3F3N2O, The compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

2-Oxo-6-(trifluoromethyl)-1,2-dihydropyridine-3-carbonitrile 1 (5.0 g, 0.03 mol) and potassium carbonate (7.3 g, 0.05 mol) were taken in dry acetone(50 mL), stirred for 30 minutes at RT, followed by the addition of propargyl bromide (3.1 g, 0.03 mol) then catalytic amount of sodium iodide (NaI) was added. The mixture was continuously stirred for 6 h at RT. The progress of the reaction was monitored by TLC, and after completion of the reaction, acetone was removed under reduced pressure. The residue was treated with ice cold water (40 mL) and the aqueous layer was extracted twice with ethyl acetate (2 × 40mL). The combined organic phases were dried over Na2SO4 and evaporated on rotavapor. The resulted residue was purified using 60-120 mesh silica gel column chromatography. Yield 81% (Yellow liquid). FTIR (Neat): 2236 (CN), 2129 (C?C), 1583 cm-1(C=N); 1H NMR (CDCl3, 300 MHz): delta 2.48 (t, 1H, J = 2.26 Hz, C?C-H), 5.14 (d, 2H, J = 2.26 Hz, OCH2), 7.41 (d, 1H, J = 7.55 Hz, Ar-H), 8.10 (d, 1H, J = 7.55 Hz, Ar-H); 13C NMR (CDCl3, 75 MHz): delta 55.53 (O-CH2), 75.90 (Acetylene-C), 76.89 (Acetylene-C), 100.68 (C-CN) 113.51 (Ar-C), 113.80 (CN), 120.27 (q, J = 273.99 Hz) (CF3), 144.93 (Ar-C), 148.81 (q, J = 34.11 Hz) (C-CF3), 162.30 (Ar-C-O); ESI-MS: m/z 227 (M+1); HRMS: m/z Calcd for C10H6F3N2O ([M+H]+): 227.0124. Found: 227.0124.

While traditionally a conservative industry, chemical producers will need to modernize their PR strategies to stay relevant.we look forward to future research findings about 116548-04-0, 2-Oxo-6-(trifluoromethyl)-1,2-dihydropyridine-3-carbonitrile.

Reference:
Article; Kumar, R. Naresh; Mallareddy; Nagender; Rao, P. Sambasiva; Poornachandra; Ranjithreddy; Kumar, C. Ganesh; Narsaiah; Indian Journal of Chemistry – Section B Organic and Medicinal Chemistry; vol. 55B; 11; (2016); p. 1361 – 1375;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 116548-04-0, With the rapid development and complex challenges of chemical substances, the synthesis of new drugs is usually one of the most effective ways to increase yield.116548-04-0, name is 2-Oxo-6-(trifluoromethyl)-1,2-dihydropyridine-3-carbonitrile, molecular formula is C7H3F3N2O, molecular weight is 188.11, as common compound, the synthetic route is as follows.

2-Oxo-6-(trifluoromethyl)-1,2-dihydropyridine-3-carbonitrile 1 (5.0 g, 0.03 mol) and potassium carbonate (7.3 g, 0.05 mol) were taken in dry acetone (50 mL), followed by the addition of propargyl bromide (3.1 g,0.03 mol), then catalytic amount of sodium iodide (NaI) was added. The mixture was continuously stirred for 6 to 10 h at reflux temperature. After completion of the reaction, the residue was treated with ice cold water. The solution was extracted with ethyl acetate, dried over anhydrous sodium sulphate and concentrated. The resulted residue was purified using 60-120 mesh silica gel column chromatography. Yield 74% (Pale yellow solid). m.p. 143-45C. FTIR(KBr): 3459, 3173 (amide, NH2), 2131 (C?C), 1693 (amide, CO), 1616 cm-1 (C=N); 1H NMR (CDCl3,300 MHz): delta 2.56 (t, 1H, J = 2.20 Hz, C?C-H), 5.20 (d, 2H, J = 2.20 Hz, OCH2), 6.10 (br, s, 1H, CONH2), 7.48 (d, 1H, J = 7.72 Hz, Ar-H), 7.68 (br, s, 1H,CONH2), 8.71 (d, 1H, J = 7.72 Hz, Ar-H); 13C NMR (CDCl3, 75 MHz): delta 54.29 (O-CH2), 75.56 (Acetylene-C), 76.77 (Acetylene-C), 113.99 (Ar-C), 118.80 (C-CO), 119.98 (q, J = 273.99 Hz) (CF3), 142.77(Ar-C), 146.29 (q, J = 34.11 Hz) (C-CF3), 158.31 (Ar-C-O), 163.02 (C=O); ESI-MS: m/z 245 (M+1); HRMS: m/z Calcd for C10H8F3N2O2 ([M+H]+): 245.0243. Found: 245.0231.

Statistics shows that 116548-04-0 is playing an increasingly important role. we look forward to future research findings about 2-Oxo-6-(trifluoromethyl)-1,2-dihydropyridine-3-carbonitrile.

Category: 116548-04-0

A new synthetic route of 2-Oxo-6-(trifluoromethyl)-1,2-dihydropyridine-3-carbonitrile

Brief introduction of 2-Oxo-6-(trifluoromethyl)-1,2-dihydropyridine-3-carbonitrile