METHYL-(3-NITRO-PYRIDIN-2-YL)-AMINE

To a solution of 3-nitro-2-chloropyridine (4.0 g, 25.2 mmol) in 15 mL 2-methoxyethanol was added methylamine (2.0 M in THF, 32 mL). The reactionwas stirred for 8 hr at 80 °C in a sealed tube. After cooling to rt, the reaction mixture was evaporated to afford 15 quantitatively (3.6 g, 23.2 mmol). 1H NMR (500 MHz, CDCl3) δ 8.47 – 8.37 (m, 2H), 8.20 (s, 1H), 6.64 (dd, J = 8.3, 4.4 Hz, 1H), 3.17 (d, J = 4.8 Hz, 3H). 13C NMR (126 MHz, CDCl3) δ 156.0, 153.5, 135.4, 111.7, 28.4. HRMS (ESI+) m/z calcd for C6H8N3O2+ 154.0617, found 154.0610.Methylamine (33percent in EtOH) (1 10 mL, 883 mmol) was placed in a 500 mL three necked round bottom flask. It was cooled to 0 °C using ice bath. 2-chloro-3-nitropyridine (20 g, 126 mmol) was added to the above solution in portions as this is an exothermic reaction. After the addition was complete the reaction mixture was stirred for 2 h at 0 °C and later 1 h at room temperature. Solvent was concentrated and residue was taken in 500 mL of water and extracted with EtOAc 3 x 150 mL. Combine organic layer was dried over Na2SC'4, filtered and concentrated to give a bright orangish yellow solid(19 g , 98.5percent).24 mL of methylamine, 39.5 mL of triethylamine was added to 240 mL of dichloromethane, and 30 g(0.18 mol) of 2-chloro-3-nitropyridine, and the reaction was completed at room temperature for 5 h. After completion of the reaction, the reaction solution was washed three times with waterInto anhydrous sodium sulfate in addition to water, suction filtration, steaming, yellow crystalline solid product 44.8g (yield 95.76percent).2-chloro-3-nitropyridine 70.0 g, 0.44 mol) was dissolved in recently distilled acetonitrile (400 mL) under stirring. Sodium acetate (55.2 g, 0.67 mol) and 30percent aqueous solution of methylamine (111 mL) were added under vigorous stirring. The obtained suspension was stirred at room temperature for 30 min, refluxed for 1 h, and kept overnight at room temperature. The yellow reaction mixture was concentrated under reduced pressure to remove approximately 300 mL of the solvent. The residue was diluted with 20percent aqueous solution of KSynthesis of N-methyl-3-nitropyridin-2-amineTo a solution of 3-nitro-2-chloropyridine (4.0 g, 25.2 mmol) in 15 mL 2-methoxyethanol was added methylamine (2.0 M in THF, 32 mL). The reactionwas stirred for 8 hr at 80 °C in a sealed tube. After cooling to rt, the reaction mixture was evaporated to afford 15 quantitatively (3.6 g, 23.2 mmol). 1H NMR (500 MHz, CDCl3) δ 8.47 – 8.37 (m, 2H), 8.20 (s, 1H), 6.64 (dd, J = 8.3, 4.4 Hz, 1H), 3.17 (d, J = 4.8 Hz, 3H). 13C NMR (126 MHz, CDCl3) δ 156.0, 153.5, 135.4, 111.7, 28.4. HRMS (ESI+) m/z calcd for C6H8N3O2+ 154.0617, found 154.0610.Methylamine (33percent in EtOH) (1 10 mL, 883 mmol) was placed in a 500 mL three necked round bottom flask. It was cooled to 0 °C using ice bath. 2-chloro-3-nitropyridine (20 g, 126 mmol) was added to the above solution in portions as this is an exothermic reaction. After the addition was complete the reaction mixture was stirred for 2 h at 0 °C and later 1 h at room temperature. Solvent was concentrated and residue was taken in 500 mL of water and extracted with EtOAc 3 x 150 mL. Combine organic layer was dried over Na2SC'4, filtered and concentrated to give a bright orangish yellow solid(19 g , 98.5percent).24 mL of methylamine, 39.5 mL of triethylamine was added to 240 mL of dichloromethane, and 30 g(0.18 mol) of 2-chloro-3-nitropyridine, and the reaction was completed at room temperature for 5 h. After completion of the reaction, the reaction solution was washed three times with waterInto anhydrous sodium sulfate in addition to water, suction filtration, steaming, yellow crystalline solid product 44.8g (yield 95.76percent).2-chloro-3-nitropyridine 70.0 g, 0.44 mol) was dissolved in recently distilled acetonitrile (400 mL) under stirring. Sodium acetate (55.2 g, 0.67 mol) and 30percent aqueous solution of methylamine (111 mL) were added under vigorous stirring. The obtained suspension was stirred at room temperature for 30 min, refluxed for 1 h, and kept overnight at room temperature. The yellow reaction mixture was concentrated under reduced pressure to remove approximately 300 mL of the solvent. The residue was diluted with 20percent aqueous solution of KSynthesis of N-methyl-3-nitropyridin-2-amine

Molecular Weight:153.14
XLogP3:1.6
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:1
Exact Mass:153.053826475
Monoisotopic Mass:153.053826475
Topological Polar Surface Area:70.7
Heavy Atom Count:11
Complexity:145
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes