Itaconic acid → 5-Oxo-1-phenylpyrrolidine-3-carboxylic acid

HRID 732663Notes

Reaction equation

HRID 732663 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:8]([OH:16])(=[O:15])[C:9]([CH2:11][C:12](O)=[O:13])=[CH2:10]>Cl>[O:13]=[C:12]1[N:1]([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH2:10][CH:9]([C:8]([OH:16])=[O:15])[CH2:11]1

Participants

4

Reactant 2

HCID 811Itaconic acidHCID 6115Aniline

Product 1

HCID 27371075-Oxo-1-phenylpyrrolidine-3-carboxylic acid

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

In accordance with the method of “Journal of the American Chemical Society”, vol. 72, 1950, p. 1415, aniline was added to an itaconic acid aqueous solution and heated under reflux for 12Hours. After completion of the reaction, this was ice-cooled and mixed with 70 ml of 1 M hydrochloric acid, and the thus precipitated crystals were collected by filtration to obtain 5-oxo-1-phenylpyrrolidine-3-carboxylic acid. EP: 206.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 12Hours
  3. customAfter completion of the reaction
  4. filtrationthe thus precipitated crystals were collected by filtration

Sources & evidence

ORD record
ord-07d2cc70a1f94326b7e699da61517154
Source dataset
uspto-grants-2009_09
Patent number
US07585886B2

Reaction notes

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