4-Pyridinecarbonitrile,1,2-dihydro-1-methyl-2-oxo-(9CI)

To a stirred solution of compound I (0.25 g; 2.08 mmol; 1 eq) in DMF (5 mL) was added sodium hydride (0.12 g; 3.12 mmol; 1.5 eq) and the resulting mixture was stirred for 10 mm at 0 °C. To the mixture was then added methyl iodide (0.4 mL; 6.25 mmol; 3 eq) and the resulting mixture was stirred at 23 °C for 2 h. The mixture was diluted with water (50 mL) and the organic components were extracted with ethyl acetate (2 x 200 mL). The combined organic layers were washed with water and brine, dried over anhydrous sodium sulfate, filtered and the solvents were removed in vacuo to obtain the title compound (0.18 g, 67percent). 1H NMR (DMSO-d6) ö 7.93 (d, iH, J = 7 Hz), 7.00 (s, iH), 6.52 (dd, iH, J = 2, 7 Hz), 3.45 (s, 3H).2-oxo-1, 2-dihydropyridin-4-carbonitrile (1.00 g), Methanol (4To 10 μL) and tetrahydrofuran (10 mL) suspension, Under ice-cooling, (Cyano-methylene)Tributylphosphorane (2.44 g)It was dropped, And the mixture was stirred for 15 hours at room temperature.It added ISOLUTE HM-N to the reaction solution, And concentrated under reduced pressure.The residue was purified by column chromatography (silica gel cartridge, Hexane: ethyl acetate = 75: 25-0: After purification at 100), The resulting solid was washed with isopropyl ether to give the title compound (771 mg) as a pale brown solid.2-oxo-1, 2-dihydropyridin-4-carbonitrile (1.00 g), Methanol (4To 10 muL) and tetrahydrofuran (10 mL) suspension, Under ice-cooling, (Cyano-methylene)Tributylphosphorane (2.44 g)It was dropped, And the mixture was stirred for 15 hours at room temperature.It added ISOLUTE HM-N to the reaction solution, And concentrated under reduced pressure.The residue was purified by column chromatography (silica gel cartridge, Hexane: ethyl acetate = 75: 25-0: After purification at 100), The resulting solid was washed with isopropyl ether to give the title compound (771 mg) as a pale brown solid.1- Methyl-2-oxo-1, 2-dihydropyridine-4-carbonitrile (302 mg), it was heated under reflux for 3 hours a mixture of 50% hydroxylamine aqueous solution (160 muL) and ethanol (2.0 mL). The reaction mixture wasconcentrated under reduced pressure to give the title compound (366 mg) as a colorless solid.[0149] To a stirred solution of compound I (0.25 g; 2.08 mmol; 1 eq) in DMF (5 mL) was added sodium hydride (0.12 g; 3.12 mmol; 1.5 eq) and the resulting mixture was stirred for 10 mm at 0 C. To the mixture was then added methyl iodide (0.4 mL; 6.25 mmol; 3 eq) and the resulting mixture was stirred at 23 C for 2 h. The mixture was diluted with water (50 mL) and the organic components were extracted with ethyl acetate (2 x 200 mL). The combined organic layers were washed with water and brine, dried over anhydrous sodium sulfate, filtered and the solvents were removed in vacuo to obtain the title compound (0.18 g, 67%). 1H NMR (DMSO-d6) oe 7.93 (d, iH, J = 7 Hz), 7.00 (s, iH), 6.52 (dd, iH, J = 2, 7 Hz), 3.45 (s, 3H).[0151] To a stirred solution of compound 11(1.67 g; 11.9 mmol; 1 eq) in methanol (80 mL) was added concentrated HC1 (1 mL) followed by 10% Pd/C (1.6 g) and the resulting mixture was stirred under hydrogen atmosphere at a pressure of 50 psi for 4 h in a Parr autoclave. The mixture was filtered through a Celite bed, washed with methanol and solvent of the filtrate was removed in vacuo to obtain the title compound (2 g, 92%). 1H NMR (DMSO-d6) oe 8.55 (brs, iH), 7.72 (d, iH, J= 7Hz), 6.46 (s, iH), 6.31 (dd, iH, J= 2, 7 Hz, ), 3.86 (m, 2H), 3.40 (s, 3H).

Molecular Weight:134.14
XLogP3:-0.2
Hydrogen Bond Acceptor Count:2
Exact Mass:134.048012819
Monoisotopic Mass:134.048012819
Topological Polar Surface Area:44.1
Heavy Atom Count:10
Complexity:267
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes