Nicotinic Acid → Succinimidyl Nicotinate

HRID 4578

Reaction equation

HRID 4578 reaction equation
[C:1]([OH:9])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[N:4][CH:3]=1.O[N:11]1[C:15](=[O:16])[CH2:14][CH2:13][C:12]1=[O:17].C1(N=C=NC2CCCCC2)CCCCC1.CCOCC>O1CCOCC1>[C:1]([O:9][N:11]1[C:15](=[O:16])[CH2:14][CH2:13][C:12]1=[O:17])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[N:4][CH:3]=1

Participants

6

Reactant 4

HCID 938Nicotinic AcidHCID 3283Diethyl EtherHCID 10868DicyclohexylcarbodiimideHCID 80170N-Hydroxysuccinimide

Product 1

HCID 870586Succinimidyl NicotinateYield 72%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

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##

Workup

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

Sources & evidence

ORD record
ord-c4b9f4b95d474b5a9a51663bf3ff7ff1
Source dataset
uspto-grants-1988_02
Patent number
US04727079

Linked notes

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