Water → 2-Methyl-3-((5-nitropyridin-2-yl)oxy)pyridine

Participants

Reaction Conditions

Reaction Steps

3-Hydroxy-2-methylpyridine (40 g, 0.37 mole) in dry DMF (1.3 L) under argon was cooled to 0° C. Sodium hydride (11.1 g of an 80% dispersion in oil, 0.37 mole) was added portionwise and the mixture stirred at 0° C. for 15 minutes and then room temperature for 3 hours. 2-Chloro-5-nitropyridine (58.6 g, 0.37 mole) was added and the mixture stirred for 18 hours at r.t. Water (50 ml) was added dropwise and the solvent was removed in vacuo. The residue was dissolved in CH2Cl2, washed with 10% aqueous sodium hydroxide, and water, dried (Na2SO4) and evaporated in vacuo to afford the title compound (81.1 g, 95%) as a yellow solid.

Provenance & Evidence