2-(Methoxycarbonyl)-3-Methylpyridine 1-oxide synthesis

Yield:878207-91-1 98%

Reaction Conditions:

with 3-chloro-benzenecarboperoxoic acid in dichloromethane at 0 - 20; for 4 h;

Steps:

2-Methoxycarbonyl-3-methylpyridine 1-oxide (1)

To a solution of methyl 3-methylpicolinate (5.0 g, 33.1 mmol) in dichloromethane (100 ml) was added of m-chloroperbenzoic acid (8.9 g, 39.7 mmol) at 0^oC. After being stirred for 4 h at room temperature, the reaction mixture was combined with 100 ml of water, extracted with dichoromethane (50 ml x 2), and washed with water and sat. sodium bicarbonate solution. The combined organic layer was dried over anhydrous sodium sulfate, and filtered. The solvent was removed from the filtrate under reduced pressure, and the resulting residue was refined by silica gel column chromatography (5% MeOH/CH₂Cl₂) to give 5.3g (yield 98%) of the title compound. ¹H NMR(300MHz, CDCl₃) δ 8.09 (d, J = 6.3 Hz, 1H), 7.12 (m, 1H), 7.13 (d, J = 7.9 Hz, 1H), 4.03 (s, 3H), 2.30 (s, 3H).

References:

Lim, Chae Jo;Kim, Ji Young;Lee, Byung Ho;Oh, Kwang-Seok;Yi, Kyu Yang [Bioorganic and Medicinal Chemistry Letters,2013,vol. 23,# 6,p. 1736 - 1739] Location in patent:supporting information