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

HRID 855575Notes

Reaction equation

HRID 855575 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]>>[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

3

Reactant 2

HCID 811Itaconic acidHCID 97314-Fluoroaniline

Product 1

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

Procedure

4-Fluoroaniline (0.7 ml, 7.6 mmol) was added to 2-methylenebutanedioic acid (1.0 g, 7.6 mmol) in a sealed tube. The mixture was heated to 110 degrees for 3 hours after which a precipitate formed. The reaction was filtered and the solid was dissolved in ethyl acetate and concetrated to yield 1-(4-fluorophenyl)-5-oxopyrrolidine-3-carboxylic acid (M+1=223.8). The product was taken to next step without determining mass.

Workup

  1. temperatureThe mixture was heated to 110 degrees for 3 hours after which a precipitate
  2. customformed
  3. filtrationThe reaction was filtered
  4. dissolutionthe solid was dissolved in ethyl acetate

Sources & evidence

ORD record
ord-fad97dd0ea5545e8af3da0439411a1be
Source dataset
uspto-grants-2007_08
Patent number
US07262198B2

Reaction notes

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