Nicotinic Acid → Succinimidyl Nicotinate

Participants

Reaction Steps

Nicotinic acid (12.3 g; 0.1 mole) and N-hydroxysuccinimide (11.5 g; 0.1 mole) are dissolved in 300 milliliters of hot dioxane. The mixture is cooled on an ice-bath and dicyclohexylcarbodiimide (20.6 g; 0.1 mole) in 30 milliliters of dioxane is added. The reaction mixture is stirred, with cooling, for approximately three hours, then refrigerated for at least 2 hours. The precipitated dicyclohexylurea is removed by filtration, the solution is condensed under vacuum, and the yellowish solids which precipitate are recrystallized from ethyl acetate. White crystals (14 g) of succinimidyl nicotinate are obtained (Yield 63.6%). Structure of the product is confirmed by NMR.

Provenance & Evidence