2-METHOXY-5-NITRO-6-PICOLINE

To intermediate 73 (1.95 g, 0.015 mol) at r. t. , was added HNO3 60percent (7ml). The mixture became reddish brown with generation of heat and NO2. CONC. H2SO4 (7ML) was then added. The solution was stirred at 80°C overnight. Into the cooled reaction mixture was poured ice water (70ml) and the solution was neutralized with CACO3. The aqueous solution was extracted with EtOAc (3X50 mL) and the combined organic extracts were dried over anh. NA2SO4. The solids were filtered and the solvent was evaporated to dryness to give the title compound (2.25 g, 86percent) as a yellow solid. NMR ('H, DMSO): 8 8.3 (d, 1H) ; 6.8 (d, 1H) ; 4 (s, 3H), 2.7 (s, 3H).Sodium metal (0.119g, 5.1mmol) was dissolved in methanol (6ml) at 0°C (ice bath), 6-chloro-2-methyl-3-nitro-pyridine (0.30g, 1.7mmol) was added and the mixture was stirred at 0°C until the complete consumption of 6-chloro-2-methyl-3-nitro-pyridine (4h). Acetic acid (0.306g, 5.1mmol) was added and the solution was concentrated under reduced pressure. The residue was dissolved in ethyl acetate (20 ml), washed with water (10 ml), dried over anhydrous Na6-methoxy-3-nitro-2-picoline 6-methoxy-3-nitro-2-picoline

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