Itaconic acid → 1-(4-Isopropylphenyl)-5-oxopyrrolidine-3-carboxylic acid
Reaction equation
[CH:1]([C:4]1[CH:10]=[CH:9][C:7]([NH2:8])=[CH:6][CH:5]=1)([CH3:3])[CH3:2].[C:11]([OH:19])(=[O:18])[C:12]([CH2:14][C:15](O)=[O:16])=[CH2:13]>[OH-].[Na+]>[CH:1]([C:4]1[CH:10]=[CH:9][C:7]([N:8]2[C:15](=[O:16])[CH2:14][CH:12]([C:11]([OH:19])=[O:18])[CH2:13]2)=[CH:6][CH:5]=1)([CH3:3])[CH3:2]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 125 °C
Procedure
A mixture of 4-isopropylaniline (0.76 g, 0.565 mmol) and itaconic acid (0.70 g, 0.538 mmol) was heated at 120-130° C. in a sealed tube for 2.5 hrs. The mixture was cooled and dissolved in 10% NaOH solution (15 ml) and stirred for 20 min. The aqueous layer was washed with ethyl acetate and acidified with dil. HCl. The precipitate was filtered to obtain 1-(4-isopropyl-phenyl)-5-oxo-pyrrolidine-3-carboxylic acid (1.0 g, 75%).
Workup
- temperatureThe mixture was cooled
- washThe aqueous layer was washed with ethyl acetate
- filtrationThe precipitate was filtered
Sources & evidence
- ORD record
- ord-3dc6c19888544f5d8690f43ceb657f86
- Source dataset
- uspto-grants-2012_08
- Patent number
- US08252797B2
Reaction notes
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