Sodium Methoxide → 4-methoxy-2-n-propylpyridine-N-oxide

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Reaction Steps

A solution of 4-nitro-2-n-propylpyridine-N-oxide (146.0 g, 0.8 mol) in 500 ml of anhydrous methanol was stirred and 190 ml of a 4.6 M methanolic sodium methoxide solution was added dropwise. When the addition was complete, the mixture was stirred for three hours. The precipitated sodium nitrite was filtered off and washed with methanol. The filtrate was evaporated and the residue was stirred with 300 ml of dichloromethane. The mixture was filtered and evaporated to afford 129 g (97%) of 4-methoxy-2-n-propylpyridine-N-oxide as an oil. 1H-NMR (CDCl3, 200 MHz) δ: 1.07 (t, 3H); 1.80 (sext, 2H); 2.80 (t, 2H); 3.87 (s, 3H); 6.66-6.78 (m, 2H); 8.17 (d, 2H).

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