Itaconic acid → 1-(4-Fluorophenyl)-5-oxopyrrolidine-3-carboxylic acid

HRID 2194835Notes

Reaction equation

HRID 2194835 reaction equation
[F:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][CH:3]=1.[CH2:9]=[C:10]([CH2:14][C:15](O)=[O:16])[C:11]([OH:13])=[O:12]>O>[F:1][C:2]1[CH:8]=[CH:7][C:5]([N:6]2[C:15](=[O:16])[CH2:14][CH:10]([C:11]([OH:13])=[O:12])[CH2:9]2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 811Itaconic acidHCID 97314-Fluoroaniline

Product 1

HCID 29126521-(4-Fluorophenyl)-5-oxopyrrolidine-3-carboxylic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
170 °C

Procedure

A 250 mL round-bottomed flask was charged with 4-fluoroaniline 50 (12.8 g, 115 mmol) and 2-methylenesuccinic acid 49 (15.0 g, 115 mmol). The flask was fitted with a reflux condenser then heated at 170° C. Once at that temperature, heating was continued for 15 min. After that time, the molten mass was cooled to room temperature and water was added. The resulting precipitate was filtered then dissolved in 2 N NaOH. The solution was filtered again and the filtrate was acidified using concentrated HCl. The resulting precipitate was collected by filtration and dried at 70° C. under vacuum to give 1-(4-fluorophenyl)-5-oxopyrrolidine-3-carboxylic acid 51.

Workup

  1. customThe flask was fitted with a reflux condenser
  2. temperatureOnce at that temperature, heating
  3. temperatureAfter that time, the molten mass was cooled to room temperature
  4. filtrationThe resulting precipitate was filtered
  5. dissolutionthen dissolved in 2 N NaOH
  6. filtrationThe solution was filtered again
  7. filtrationThe resulting precipitate was collected by filtration
  8. customdried at 70° C. under vacuum

Sources & evidence

ORD record
ord-6c5fd976677e4c61904f129634c5d82e
Source dataset
uspto-grants-2012_12
Patent number
US08334317B2

Reaction notes

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