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

HRID 715921Notes

Reaction equation

HRID 715921 reaction equation
[Br:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][CH:3]=1.[C:9]([OH:17])(=[O:16])[C:10]([CH2:12][C:13](O)=[O:14])=[CH2:11]>CCCCCC.C(OCC)(=O)C>[Br:1][C:2]1[CH:8]=[CH:7][C:5]([N:6]2[C:13](=[O:14])[CH2:12][CH:10]([C:9]([OH:17])=[O:16])[CH2:11]2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 811Itaconic acidHCID 78074-Bromoaniline

Product 1

HCID 29122081-(4-bromophenyl)-5-oxopyrrolidine-3-carboxylic acidYield 95.1%

Reagents, catalysts & solvents 1

HCID 21226206Ethyl acetate hexaneSolvent

Conditions

Temperature
130 °C

Procedure

A mixture of 4-bromoaniline (8.6 g) and itaconic acid (6.5 g) was stirred at 130° C. for 50 minutes. After cooling, a n-hexane-ethyl acetate mixed solution was added to the resulting solid. The compound was collected by filtration to obtain the title compound (13.5 g).

Workup

  1. temperatureAfter cooling
  2. filtrationThe compound was collected by filtration

Sources & evidence

ORD record
ord-ccaf1d096ab048188b6f2084bb2a7bb1
Source dataset
uspto-grants-2015_11
Patent number
US09187489B2

Reaction notes

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