Nicotinic Acid → Succinimidyl Nicotinate

HRID 1089002Notes

Reaction equation

HRID 1089002 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 recrystalized 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 recrystalized from ethyl acetate

Sources & evidence

ORD record
ord-13b9133ff8f04259991f8518ac333f21
Source dataset
uspto-grants-1990_10
Patent number
US04963688

Reaction notes

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