Itaconic acid → HCID 13422553, compound
Reaction equation
[C:1]([OH:9])(=[O:8])[C:2]([CH2:4][C:5]([OH:7])=O)=[CH2:3].[CH3:10][O:11][C:12]1[CH:13]=[C:14]([CH:17]=[CH:18][C:19]=1[O:20][CH3:21])[CH2:15][NH2:16]>[OH-].[Na+]>[CH3:10][O:11][C:12]1[CH:13]=[C:14]([CH:17]=[CH:18][C:19]=1[O:20][CH3:21])[CH2:15][N:16]1[CH2:3][CH:2]([C:1]([OH:9])=[O:8])[CH2:4][C:5]1=[O:7]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 130 °C
Procedure
A mixture of 6.0 g (46 mmols) of itaconic acid and 7.7 g (46 mmols) of 3,4-dimethoxybenzylamine was heated at 130° C. for 2 hours in a nitrogen atmosphere. After cooling to about 100° C., 70 ml of 10% sodium hydroxide were added to the viscous reaction mixture, while mechanically stirring, and the resulting mixture was then cooled to room temperature. In order to remove any insoluble matter, the sodium salt solution was extracted with 50 to 100 ml of ethyl acetate, and the aqueous phase was acidified with dilute hydrochloric acid. The oil precipitated thereby was taken up in methylene chloride, and the methylene chloride phase was dried and concentrated by evaporation. The residue crystallized when ether was added. 8.7 g (68% of theory) of 1-(3,4-dimethoxybenzyl)-4-carboxy-pyrrolidin-2-one were obtained. Melting point: 176°-178° C.
Workup
- temperatureAfter cooling to about 100° C.
- temperaturethe resulting mixture was then cooled to room temperature
- customIn order to remove any insoluble matter
- extractionthe sodium salt solution was extracted with 50 to 100 ml of ethyl acetate
- customThe oil precipitated
- dry with materialthe methylene chloride phase was dried
- concentrationconcentrated by evaporation
- customThe residue crystallized when ether
- additionwas added
Sources & evidence
- ORD record
- ord-27ff0bb88ff34c7c95f307bb9beb53bf
- Source dataset
- uspto-grants-1986_04
- Patent number
- US04581364
Reaction notes
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