ChemicalBook CAS DataBase List 2-Methyl-3-nitropyridine N-oxide

2-Methyl-3-nitropyridine N-oxide synthesis

6synthesis methods

Product Name:2-Methyl-3-nitropyridine N-oxide
CAS Number:5236-76-0
Molecular formula:C6H6N2O3
Molecular Weight:154.12

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Yield:5236-76-0 81%

Reaction Conditions:

with 3-chloro-benzenecarboperoxoic acid in dichloromethane at 20; for 6 h;

Steps:

9

Example 9; Synthesis of 3-amino-1-hydroxy-3,4-dihydro-1,5-naphthyridin-2(1H)-one, dihydrochloride salt (50); 2-Methyl-3-nitropyridine 1-oxide (44); To a solution of 2-methyl-3-nitropyridine (43) (0.86 g, 6.23 mmol) in DCM (30 mL) was added mCPBA (2.8 g, 12.5 mmol). The reaction was then allowed to stir at RT for 6 h. Sodium thiosulfate (900 mg) was added and the mixture was allowed to stir overnight. The reaction mixture was diluted with additional DCM and washed with a saturated aqueous NaHCO₃solution. The organic layer was dried over magnesium sulfate, filtered and concentrated in vacuo. The residue was purified by chromatography on silica gel (Gradient: 0% to 20% MeOH in DCM) to afford the product (782 mg, 81%). LCMS m/z 155.0 (M+1). ¹H NMR (400 MHz, CDCl₃) δ 2.73 (m, 3H), 7.30 (br dd, J=8.1, 6.8 Hz, 1H), 7.72 (dq, J=8.4, 0.5 Hz, 1H), 8.48 (dq, J=6.6, 0.6 Hz, 1H).

References:

US2010/324043,2010,A1 Location in patent:Page/Page column 32-33

64362-41-0 Synthesis