Itaconic acid → 5-Oxo-1-p-tolyl-pyrrolidine-3-carboxylic acid

HRID 1885620Notes

Reaction equation

HRID 1885620 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][CH:3]=1.[C:9]([OH:17])(=[O:16])[C:10]([CH2:12][C:13](O)=[O:14])=[CH2:11]>O>[C:5]1([CH3:8])[CH:6]=[CH:7][C:2]([N:1]2[C:13](=[O:14])[CH2:12][CH:10]([C:9]([OH:17])=[O:16])[CH2:11]2)=[CH:3][CH:4]=1

Participants

4

Reactant 2

HCID 811Itaconic acidHCID 7813p-Toluidine

Product 1

HCID 27418275-Oxo-1-p-tolyl-pyrrolidine-3-carboxylic acidYield 97%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
130 °C

Procedure

p-Toluidine (23.05 g) and itaconic acid (28.0 g) are mixed and heated at 130° C. for 1 hour to melt and then allowed to cool. Water (200 ml) is added thereto and the reaction mixture is crushed. The resulting precipitate is collected by filtration, washed with water and recrystallized from a mixed solvent (about 300 ml) of ethyl acetate and hexane [1:3 (v/v)] to give the desired product (45.73 g), m.p. 185°-187° C.

Workup

  1. temperatureto cool
  2. customthe reaction mixture is crushed
  3. filtrationThe resulting precipitate is collected by filtration
  4. washwashed with water
  5. customrecrystallized from a mixed solvent (about 300 ml) of ethyl acetate and hexane [1:3 (v/v)]

Sources & evidence

ORD record
ord-1e2689d4f28b4488baa072422dc78a0e
Source dataset
uspto-grants-1992_09
Patent number
US05145865

Reaction notes

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