O-Toluidine → N,N-diethyl-2-(o-tolylamino)nicotinamide

Participants

Reaction Conditions

Reaction Steps

To a solution of 2-chloro-N,N-diethylnicotinamide (10.0 g, 47.2 mmol) and o-toluidine (5.0 g, 47.2 mmol) in 1,4-Dioxane (50 mL) was added sodium hydride (60%, 4.72 g, 118 mmol). After addition, the reaction mixture was heated at 100° C. for 2 hours. The reaction mixture was then cooled to room temperature, diluted with dichloromethane (100 mL), washed with water (3×50 mL), dried over sodium sulfate and concentrated under reduced pressure. The crude product was purified by flash chromatography (SiO2, 50% hexane in ethyl acetate) to afford the desired product, N,N-diethyl-2-(o-tolylamino)nicotinamide (6.0 g) as a yellow oil. LCMS: 284 [M+H].

Provenance & Evidence