Itaconic acid → HCID 86658305, compound

HRID 2402762Notes

Reaction equation

HRID 2402762 reaction equation
[C:1]([OH:9])(=[O:8])[C:2]([CH2:4][C:5]([OH:7])=[O:6])=[CH2:3].CN.C(C1C[N:18](C)[C:17](=O)C1)(O)=O>O>[C:1]([OH:9])(=[O:8])[C:2]([CH2:4][C:5]([OH:7])=[O:6])=[CH2:3].[CH3:17][NH2:18]

Participants

5

Reactant 3

HCID 811Itaconic acid2×HCID 6329MethylamineHCID 1227661-Methyl-5-oxopyrrolidine-3-carboxylic acid

Product 1

HCID 86658305HCID 86658305, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Itaconic acid (100 g, 0.78 mol) and methylamine (41% in water, 60.0 g based on the aqueous solution, 0.80 mol, 1.0 equivalent) were mixed as in example 8. The suspension was heated to boiling under reflux at standard pressure for 1 hour (in the course of which the boiling point rises to approx. 115° C.). This dissolved the solids completely. Cooling to ambient temperature formed a precipitate. NMR analysis of the homogeneous solution and of the precipitated crystals (solvent: D2O) showed that the itaconic acid:4-carboxy-1-methylpyrrolidone ratio in both phases was 0:100. The 4-carboxy-1-methylpyrrolidone product was purified by recrystallization from ethyl acetate and was obtained in the form of colorless crystals (yield: 59 g, 67%).

Workup

  1. additionwere mixed as in example 8
  2. temperatureThe suspension was heated
  3. temperatureunder reflux at standard pressure for 1 hour (in the course of which the boiling point
  4. customrises to approx. 115° C.
  5. dissolutionThis dissolved the solids completely
  6. customformed a precipitate
  7. customThe 4-carboxy-1-methylpyrrolidone product was purified by recrystallization from ethyl acetate

Sources & evidence

ORD record
ord-6eb2071a5ea64ffb98dd51b68213eff3
Source dataset
uspto-grants-2014_08
Patent number
US08796472B2

Reaction notes

Loading…