Hydrochloric Acid → 1-Nonanoylpyrrolidine-2,5-dione

HRID 2255870Notes

Reaction equation

HRID 2255870 reaction equation
[C:1]1(=[O:7])[NH:5][C:4](=[O:6])[CH2:3][CH2:2]1.[C:8](Cl)(=[O:17])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16].Cl>N1C=CC=CC=1>[C:8]([N:5]1[C:4](=[O:6])[CH2:3][CH2:2][C:1]1=[O:7])(=[O:17])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 11439SuccinimideHCID 69819Nonanoyl chloride

Product 1

HCID 219471391-Nonanoylpyrrolidine-2,5-dioneYield 65.4%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

20 g succinimide were suspended in 100 ml pyridine, 0.5 g N,N-dimethylaminopyridine added, and 39.2 g nonanoic acid chloride added dropwise at ice-bath temperature. Subsequently the mixture was stirred for 1 h at room temperature and 500 ml of 2N HCl solution were added with cooling. The aqueous phase was extracted with ethyl acetate and the organic phase washed with 2N HCl solution and dried (Na2SO4). After removing the solvent, the residue was twice recrystallized from n-hexane. 31.6 g (65%) N-nonanoylsuccinimide were obtained as a colourless solid. Melting point: 59 to 60° C. (n-hexane). The 1H-NMR spectroscopic data are in agreement with the structure.

Workup

  1. temperaturewith cooling
  2. extractionThe aqueous phase was extracted with ethyl acetate
  3. washthe organic phase washed with 2N HCl solution
  4. dry with materialdried (Na2SO4)
  5. customAfter removing the solvent
  6. customthe residue was twice recrystallized from n-hexane

Sources & evidence

ORD record
ord-1d0ab5015ac44e80bfb4e291e1b0f0fe
Source dataset
uspto-grants-1997_08
Patent number
US05654269

Reaction notes

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