Methanol → 2-Methoxy-5-methyl-3-nitropyridine

Beteiligte Stoffe

Reaktionsschritte

To a solution of sodium (2.31 g, 0.1 mol) dissolved in methanol (100 mL) at room temperature, 2-chloro-5-methyl-3-nitro-pyridine (17.2 g, 0.1 map was added. The reaction mixture was refluxed for 4 h under N2 atmosphere. After evaporated to dryness, the residue was diluted with water (100 mL) and extracted (2×50 mL CH2Cl2). The combined extracts were washed with brine, dried on MgSO4, and filtered. The solvent was evaporated and the residue was crystallized from a mixture of water (300 mL) and ethanol (20 mL) to yield 2-methoxy-5-methyl-3-nitro-pyridine as a light orange solid (15.4 g, 92%). 1H-NMR (DMSO-d6): δ 2.31 (s, 3H, CH3), 3.98 (s, 3H, OCH3), 8.30 (d, 1H, J=2.0 Hz, Py-H), 8.35 (d, 1H, J=2.0 Hz, Py-H); 13C-NMR (DMSO-d6): δ 16.80, 54.86, 127.36, 133.7, 135.91, 152.03, 154.27; HR-MS (ESI+) m/z 169.0570 [M+H]+; C7H8N2O3 requires 168.0535.

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