Reacción #4674

Ecuación de reacción

ether

Nicotinic acid

N-hydroxysuccinimide

Dicyclohexylcarbodiimide

→

N-Nicotinoyloxysuccinimide

Rendimiento 72.0%

Disolventes

dioxane

dioxane

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroThe dicyclohexylurea which precipitated
2. 2
   Otrowas removed by filtration
3. 3
   Otrothe solvent was removed by rotary evaporation
4. 4
   OtroThe crude product was recrystallized from ethyl acetate
5. 5
   Otroto give light yellow crystals which
6. 6
   OtroThe product, obtained in 72% yield (5.2 g) and melting at 129°-131° C.

Procedimiento

Nicotinic acid (4.025 g, 0.0327 mol) and N-hydroxysuccinimide (3.763 g, 0.0327 mol) were dissolved in 130 ml of dioxane. Dicyclohexylcarbodiimide (6.75 g, 0.032 mol) in 20 ml of dioxane was added. The reaction mixture was then stirred at room temperature for 3 hours. The dicyclohexylurea which precipitated was removed by filtration and the solvent was removed by rotary evaporation. The crude product was recrystallized from ethyl acetate to give light yellow crystals which were then waashed with anhydrous ether. The product, obtained in 72% yield (5.2 g) and melting at 129°-131° C., has the formula: ##STR40##

Fuente