2-METHOXY-3-NITRO-4-PICOLINE

A solution of 2-chloro-4-methyl-3 -nitropyridine (250 g, 1.45 mol) in methanol (1.0 L) was added dropwise (2 h) to a stirred and cooled (0 °C) solution of sodium methoxide (250 g, 4.63 mol) in methanol (850 mL). After addition, the mixture was heated to reflux for 23 h, at which time TLC indicated the reaction had gone to completion. The mixture was concentrated under reduced pressure to a volume of approximately 900 mL, and quenched by addition of water (1.5 L). The resulting solid was collected by filtration, washed with water and dried under reduced pressure to give the title compound (250 g, 100percent yield) as a brownsolid. ‘H NMR (400 MHz, DMSO-d6): 8.22 (d, J= 5.2 Hz, 1 H), 7.10 (d, J= 5.6 Hz, I H), 3.92 (s, 3 H), 2.26 (s, 3 H).A solution of 2-chloro-4-methyl-3 -nitropyridine (250 g, 1.45 mol) in methanol (1.0 L) was added dropwise (2 h) to a stirred and cooled (0 °C) solution of sodium methoxide (250 g, 4.63 mol) in methanol (850 mL). After addition, the mixture was heated to reflux for 23 h, at which time TLC indicated the reaction had gone to completion. The mixture was concentrated under reduced pressure to a volume of approximately 900 mL, and quenched by addition of water (1.5 L). The resulting solid was collected by filtration, washed with water and dried under reduced pressure to give the title compound (250 g, 100percent yield) as a brown solid. NMR (400 MHz, DMSO-A solution of 2-chloro-4-methyl-3-nitropyridine (250 g, 1.45 mol) in methanol (1.0 L) was added dropwise (2 h) to a stirred and cooled (0 °C) solution of sodium methoxide (250 g, 4.63 mol) in methanol (850 mL). After addition, the mixture was heated to reflux for 23 h, at which time TLC indicated the reaction had gone to completion. The mixture was concentrated under reduced pressure to a volume of approximately 900 mL, and quenched by addition of water (1.5 L). The resulting solid was collected by filtration, washed with water and dried under reduced pressure to give the title compound (250 g, 100percent yield) as a brown solid. A solution of 2-chloro-4-methyl-3 -nitropyridine (250 g, 1.45 mol) in MeOH (1.0 L) was added dropwise over 2 h to a stirred and cooled (0 °C) solution of NaOMe (250 g, 4.63 mol) in MeOH (850 mL). The reaction was heated to reflux temperature for 23 h. The mixture was partially concentrated under reduced pressure and quenched by the addition of water (1.5 L), the resulting solid was collected by filtration, washed with water and dried under vacuum to give the titlecompound (250 g, 100percent yield) as a brown solid. ‘H NMR (400 MHz, DMSO-d6): ö 8.22 (d, J5.2 Hz, 1 H), 7.10 (d, J= 5.6 Hz, 1 H), 3.92 (s, 3 H), 2.26 (s, 3 H).

Molecular Weight:168.15
XLogP3:1.4
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:1
Exact Mass:168.05349212
Monoisotopic Mass:168.05349212
Topological Polar Surface Area:67.9
Heavy Atom Count:12
Complexity:169
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes