ChemicalBook CAS DataBase List 3,4-DIMETHOXY-2-METHYLPYRIDINE N-OXIDE

3,4-DIMETHOXY-2-METHYLPYRIDINE N-OXIDE synthesis

11synthesis methods

Product Name:3,4-DIMETHOXY-2-METHYLPYRIDINE N-OXIDE
CAS Number:72830-07-0
Molecular formula:C8H11NO3
Molecular Weight:169.18

124-41-4 Synthesis

124-41-4
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122307-41-9 Synthesis

4-Chloro-3-methoxy-2-methylpyridine N-oxide

122307-41-9
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Yield: 88%

Reaction Conditions:

in methanol at 40; for 16 h;

Steps:

3,4-Dimethoxy-2-methylpyridine N-Oxide
A mixture of 4-chloro-3-methoxy-2-methylpyridine N-Oxide, (9.0 g, 50.0 mmol) and sodium methoxide (5.4 g, 100.0mmol) in dry methanol (150 mL) was stirred at 40 ^oC for 16 h. Aftercooling, the solution was adjusted to pH 7 by addition of concentrated sulfuricacid. The mixture was evaporated in vacuo and the residue extracted withtoluene (100 mL). Afterfiltration, to remove insoluble inorganic salts, the filtrate was evaporated invacuo to afford a yellow oil. Chromatography (silica gel, DCM/MeOH) followed bytrituration with petroleum ether at 40^oC afforded the desired compound (10.4 g, 88%). ¹H NMR (CDCl₃) d 8.09 (d, 1 H, J = 7.28 Hz), 6.71 (d, 1H, J =7.28 Hz), 3.92 (s, 3H), 3.85 (s, 3 H), 2.50 (s, 3 H). m/z (ESI) 170.19 (M⁺+1).

References:

Maharvi, Ghulam M.;Bharucha, Adil E.;Fauq, Abdul H. [Bioorganic and Medicinal Chemistry Letters,2013,vol. 23,# 9,p. 2808 - 2811] Location in patent:supporting information

107512-35-6 Synthesis