Nicotinic Acid → Succinimidyl Nicotinate

HRID 621698Notes

Reaction equation

HRID 621698 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>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

5

Reactant 3

HCID 938Nicotinic AcidHCID 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 are then washed with anhydrous ether. The product, obtained in 72% yield (5.2 g) and melting at 129°-131° C., has the formula: ##STR1619##

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. washare then washed with anhydrous ether
  7. customThe product, obtained in 72% yield (5.2 g) and melting at 129°-131° C.

Sources & evidence

ORD record
ord-3b3bd7d6814d4daaa85e27480c7b75d7
Source dataset
uspto-grants-1989_04
Patent number
US04824850

Reaction notes

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