Water → 2-(Pyridin-2-ylmethoxy)-5-nitropyridine

Participants

Reaction Conditions

Reaction Steps

2-Pyridylcarbinol (7.5 g, 0.069 mole) in dry dimethylformamide (190 ml) was cooled to −20° C. and treated with an 80% dispersion of sodium hydride in mineral oil (2.07 g, 0.069 mole) under argon. The mixture was stirred at −20° C. for two hours. 2-Chloro-5-nitropyridine (8.83 g, 0.058 mole) was added and the mixture was stirred at −20° C. for 0.5 hour then warmed to room temperature and stirred for 18 hours. Water was added dropwise and the solvent removed in vacuo. The residue was dissolved in dichloromethane, washed with 10% aqueous sodium hydroxide solution followed by water, dried (Na2SO4) and evaporated in vacuo to afford the title compound (12.2 g, 91%) as an orange solid.

Provenance & Evidence