Nicotinic Acid → Succinimidyl Nicotinate

HRID 1982162Notes

Reaction equation

HRID 1982162 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>CN(C)C=O>[CH2:14]1[C:15](=[O:16])[N:11]([O:8][C:1]([C:2]2[CH:7]=[CH:6][CH:5]=[N:4][CH:3]=2)=[O:9])[C:12](=[O:17])[CH2:13]1

Participants

5

Reactant 3

HCID 938Nicotinic AcidHCID 10868DicyclohexylcarbodiimideHCID 80170N-Hydroxysuccinimide

Product 1

HCID 870586Succinimidyl Nicotinate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

The title compound is prepared in known a manner from 30.8 g of nicotinic acid, 34.5 g of N-hydroxysuccinimide and 55 g of dicyclohexyl carbodiimide in 800 ml of dimethyl formamide. When the reaction is terminated, the mixture is concentrated in vacuo to one third of its volume, cooled to 0° C., filtered and the filtrate is evaporated to dryness in vacuo. The residue is recrystallized from 200 ml of isopropanol. Yield 49.0 g, melting point 137° to 138° C.

Workup

  1. customWhen the reaction is terminated
  2. concentrationthe mixture is concentrated in vacuo to one third of its volume
  3. filtrationfiltered
  4. customthe filtrate is evaporated to dryness in vacuo
  5. customThe residue is recrystallized from 200 ml of isopropanol

Sources & evidence

ORD record
ord-1d6eeb4bcc914c2d83e10bb5740455d1
Source dataset
uspto-grants-1986_06
Patent number
US04595675

Reaction notes

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