4-Nitropyridine N-oxide → 4-Ethoxypyridine n-oxide

Participants

Reaction Conditions

Reaction Steps

To a mixture of 4-nitropyridine 1-oxide (28 g, 200 mmol) in THF (50 mL) was added sodium ethanolate (40.8 g, 600 mmol). The mixture was stirred at 25° C. for 16 h. The reaction residue was then concentrated and the crude material was purified by silica column chromatography (DCM/MeOH=25:1). All fractions found to contain product by TLC (DCM/MeOH=25:1, Rf=0.6) were combined and concentrated to yield a dark red solid of 4-ethoxypyridine 1-oxide (20 g, 101 mmol, 50% yield). 1H NMR (400 MHz, MeOH-d4) δ 8.20 (d, J=7.6 Hz, 2H), 7.12 (d, J=7.6 Hz, 2H), 4.18 (q, J=7.2 Hz, 2H), 1.42 (t, J=6.8 Hz, 3H); ES-LCMS m/z: 140.0 (M+H).

Provenance & Evidence