3-Carboxy-5-(4-chlorobenzoyl)-1,4-dimethyl-1H-pyrrole-2-acetic acid → Zomepirac

HRID 1758806Notes

Reaction equation

HRID 1758806 reaction equation
[Cl:1][C:2]1[CH:23]=[CH:22][C:5]([C:6]([C:8]2[N:12]([CH3:13])[C:11]([CH2:14][C:15]([OH:17])=[O:16])=[C:10](C(O)=O)[C:9]=2[CH3:21])=[O:7])=[CH:4][CH:3]=1>FC(F)(F)C(O)=O>[Cl:1][C:2]1[CH:23]=[CH:22][C:5]([C:6]([C:8]2[N:12]([CH3:13])[C:11]([CH2:14][C:15]([OH:17])=[O:16])=[CH:10][C:9]=2[CH3:21])=[O:7])=[CH:4][CH:3]=1

Participants

3

Reactant 1

HCID 1184623-Carboxy-5-(4-chlorobenzoyl)-1,4-dimethyl-1H-pyrrole-2-acetic acid

Product 1

HCID 5733ZomepiracYield 91%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

Two hundred and thirty-five milligrams of 5-(p-chlorobenzoyl)-1,4-dimethyl-3-hydroxycarbonyl-pyrrole-2-acetic acid is dissolved in 5 ml of trifluoroacetic acid and the resulting solution is heated to reflux for 1.5 hours. After most of the solvent is removed in vacuo, the residue is treated with 10 ml of water. The resulting residue is filtered and dried in vacuo to give 5-(p-chlorobenzoyl)-1,4-dimethyl-pyrrole-2-acetic acid (Zomepirac) in 91% yield, m.p. 184°-185° C.

Workup

  1. temperaturethe resulting solution is heated
  2. temperatureto reflux for 1.5 hours
  3. customAfter most of the solvent is removed in vacuo
  4. additionthe residue is treated with 10 ml of water
  5. filtrationThe resulting residue is filtered
  6. customdried in vacuo

Sources & evidence

ORD record
ord-b004d4c5b7a6403b8b18350a507d189c
Source dataset
uspto-grants-1983_02
Patent number
US04374997

Reaction notes

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