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

HRID 58553

Reaction equation

HRID 58553 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:8]=[C:9]([CH2:13][C:14](O)=[O:15])[C:10]([OH:12])=[O:11].[OH-].[Na+]>O>[O:15]=[C:14]1[N:1]([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH2:8][CH:9]([C:10]([OH:12])=[O:11])[CH2:13]1

Participants

5

Reactant 3

HCID 811Itaconic acidHCID 6115AnilineHCID 14798Sodium Hydroxide

Product 1

HCID 27371075-Oxo-1-phenylpyrrolidine-3-carboxylic acidYield 97.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of aniline (3.26 g; 34.68 mmol) and 2-methylenesuccinic acid (5.47 g; 41.62 mmol) in water (10 mL) was heated in a sealed tube at 110° C. for 30 hours. After cooling to room temperature, 6N NaOH (13 mL) was added and the resulting precipitate was filtered off. The filtrate was acidified with 6N hydrochloric acid to pH 1 and the resulting precipitate was filtered, washed with water, and dried to yield 6.92 g (97%) of 5-oxo-1-phenypyrrolidine-3-carboxylic acid as a white solid.

Workup

  1. temperatureAfter cooling to room temperature
  2. filtrationthe resulting precipitate was filtered off
  3. filtrationthe resulting precipitate was filtered
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-d68ca60354664ce887cd2a0f418b1a7e
Source dataset
uspto-grants-2016_09
Patent number
US09434722B2

Linked notes

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