Nicotinic Acid → Succinimidyl Nicotinate

HRID 466299

Reaction equation

HRID 466299 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 63.6%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

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.

Workup

  1. temperatureThe mixture is cooled on an ice-bath
  2. temperaturewith cooling, for approximately three hours
  3. waitrefrigerated for at least 2 hours
  4. customThe precipitated dicyclohexylurea is removed by filtration
  5. customcondensed under vacuum
  6. customthe yellowish solids which precipitate are recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-b01c7bc7847941a58082d67743a4a844
Source dataset
uspto-grants-1992_10
Patent number
US05155227

Linked notes

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