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

HRID 1993374Notes

Reaction equation

HRID 1993374 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([NH2:10])[CH:5]=[CH:6][C:7]=1[O:8][CH3:9].[C:11]([OH:19])(=[O:18])[C:12]([CH2:14][C:15](O)=[O:16])=[CH2:13]>CO>[F:1][C:2]1[CH:3]=[C:4]([N:10]2[C:15](=[O:16])[CH2:14][CH:12]([C:11]([OH:19])=[O:18])[CH2:13]2)[CH:5]=[CH:6][C:7]=1[O:8][CH3:9]

Participants

4

Reactant 2

HCID 811Itaconic acidHCID 5811103-Fluoro-4-methoxyaniline

Product 1

HCID 433803921-(3-Fluoro-4-methoxyphenyl)-5-oxopyrrolidine-3-carboxylic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of 3-fluoro-4-methoxybenzenamine (7.5 g, 0.053 mmol) and itaconic acid (6.9 g, 0.053 mmol) was heated to 110° C. for 2 h. The yellow solid was dissolved in 100 mL of MeOH and concentrated in vacuo. The resulting solid was washed with 50% EtOAc/hexanes to give the title compound as a light yellow solid. MS (ESI pos. ion) m/z: 254.2 (M+H). Calc'd Exact Mass for C12H12FNO4: 253.23.

Workup

  1. concentrationconcentrated in vacuo
  2. washThe resulting solid was washed with 50% EtOAc/hexanes

Sources & evidence

ORD record
ord-e0ff7c67b1374d75be1e30dc1f87edb3
Source dataset
uspto-grants-2010_01
Patent number
US07652009B2

Reaction notes

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