2-Aminopyridine → (5-Fluoro-2-nitrophenyl)pyridin-2-yl-amine

Participants

Reaction Conditions

Reaction Steps

Prep 2: Sodium hydride (48.6 g, 60% by wt, 1.22 mol) was added piecewise to a solution of 2-aminopyridine (57.2 g, 0.61 mol) in THF (400 mL) at 0° C. at such a rate that T≦18° C. The reaction mixture was stirred at 0° C. for 10 min. then added via cannula to a solution of 2,4-difluoronitrobenzene in THF (350 mL) at −20° C. at such a rate that T≦10° C. The reaction was stirred at −40° C. for 1 h then allowed to warm to RT. As the reaction reached RT the temperature rose rapidly to 35° C. and effervescence was observed. The reaction mixture was poured onto ice (˜2 L) and the solid which formed collected by filtration. The solid was washed with pentane and dried in vacuo to give the (5-fluoro-2-nitrophenyl)pyridin-2-yl-amine as a bright orange solid (139.3 g, 94%).

Provenance & Evidence