Isonicotinic Acid → 2,5-Pyrrolidinedione, 1-[(4-pyridinylcarbonyl)oxy]-

HRID 1368953Notes

Reaction equation

HRID 1368953 reaction equation
[C:1]([OH:9])(=[O:8])[C:2]1[CH:7]=[CH:6][N:5]=[CH:4][CH:3]=1.O[N:11]1[C:15](=[O:16])[CH2:14][CH2:13][C:12]1=[O:17]>C1COCC1>[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][N:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 5922Isonicotinic AcidHCID 80170N-Hydroxysuccinimide

Product 1

HCID 27548292,5-Pyrrolidinedione, 1-[(4-pyridinylcarbonyl)oxy]-Yield 98.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of isonicotinic acid (3 g), N-hydroxysuccinimide (2.79 g) and N,N-dicyclohexylcarbodiimide (5.52 g) was stirred in THF (200 mL) for 16 hours. The solid was filtered off and the solvent evaporated under reduced pressure. The residue was triturated with ethyl acetate and more solid filtered off. The filtrates were concentrated under reduced pressure gave 2,5-dioxopyrrolidin-1-yl isonicotinate (5.27 g). MS: 221 [MH]+.

Workup

  1. filtrationThe solid was filtered off
  2. customthe solvent evaporated under reduced pressure
  3. customThe residue was triturated with ethyl acetate and more solid
  4. filtrationfiltered off
  5. concentrationThe filtrates were concentrated under reduced pressure

Sources & evidence

ORD record
ord-484efae79cfc4124ad2aa9afdd3a06d9
Source dataset
uspto-grants-2003_06
Patent number
US06576630B1

Reaction notes

Loading…