2-Pyridinecarboxylic acid, 6-chloro-3-methyl-, methyl ester

A solution of 2-(methoxycarbonyl)-3-methylpyridin-1-ium-1-olate (500 mg, 2.99 mmol, 1.00 equiv) in phosphorus oxychloride (2 mL) was stirred for 4 hours at 110° C. A solution of 2-(methoxycarbonyl)-3-methylpyridine 1-oxide (500 mg, 2.99 mmol) and phosphorus oxychloride (0.55 mL, 5.98 mmol) in 1, 2-dichloroethane (10 ml) was refluxed for 4 h. After completion of reaction, the reaction mixture was combined with 100 ml of ice water and extracted with dichoromethane (50 ml x 2) being washed with water and sodium bicarbonate solution, and then the combined organic layer was dried over anhydrous sodium sulfate, and filtered. The solvent was removed under reduced pressure, and the resulting residue was purified by silica gel column chromatography (10percent EA/Hexnae) to give 223 mg (yield 40percent) of the title compound. A solution of 2-(methoxycarbonyl)-3-methylpyridine 1-oxide (2 g, 6.0 mmol) in POCI3 (5 mL) was stirred at 100°C for 3 hours. After being concentrated, the residue was purified by column chromatography (PE : EtOAc = 1 : 1) to give the product of methyl 6-chloro- 3-methylpicolinate (380 mg, yield: 37percent). -NMR (CDCIsolution of 2-(methoxycarbonyl)-3-methylpyridine 1-oxide (2 g, 6.0 mmol) in POd3 (5 mL) was stirred at 100°C for 3 hours. After being concentrated, the residue was purified by column chromatography (PE : EtOAc = 1: 1) to give the product of methyl 6-chloro-3- methylpicolinate (380 mg, yield: 37percent). ‘H-NMR (CDC13, 400 MHz) 7.59 (d, J 8.0 Hz, 1H), 7.38 (d, J= 8.0 Hz, 1H), 3.96 (s, 3H), 2.56 (s, 3H). MS (M+H): 186 / 188.POCl

Molecular Weight:185.61
XLogP3:2.4
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:2
Exact Mass:185.0243562
Monoisotopic Mass:185.0243562
Topological Polar Surface Area:39.2
Heavy Atom Count:12
Complexity:174
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes