Ethanol → Zomepirac

HRID 1605273Notes

Reaction equation

HRID 1605273 reaction equation
[Cl:1][C:2]1[CH:22]=[CH:21][C:5]([C:6]([C:8]2[N:12]([CH3:13])[C:11]([CH2:14][C:15]([O:17]CC)=[O:16])=[CH:10][C:9]=2[CH3:20])=[O:7])=[CH:4][CH:3]=1.C(O)C>[OH-].[Na+].O>[Cl:1][C:2]1[CH:22]=[CH:21][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[CH3:20])=[O:7])=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 702EthanolHCID 118463ethyl 5-(4-chlorobenzoyl)-1,4-dimethyl-1H-pyrrole-2-acetate

Product 1

HCID 5733Zomepirac

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 14798Sodium HydroxideSolvent

Procedure

A solution of 0.01 mole of ethyl 5-(p-chlorobenzoyl)-1,4-dimethylpyrrole-2-acetate in 12 ml. (0.012 mole) of IN sodium hydroxide solution and 5 ml. of 95% ethanol is refluxed for 30 minutes. The solution is diluted with water and the ethanol evaporated in vacuo. The remaining solution is filtered and the filtrate acidified with dilute HCl. The precipitated solid is collected by filtration and recrystallized from methanol-water to yield the product, 5-(p-chlorobenzoyl)-1,4-dimethylpyrrole-2-acetic acid.

Workup

  1. customthe ethanol evaporated in vacuo
  2. filtrationThe remaining solution is filtered
  3. filtrationThe precipitated solid is collected by filtration
  4. customrecrystallized from methanol-water

Sources & evidence

ORD record
ord-7941d64fe96040dfa4e1b19a261c87db
Source dataset
uspto-grants-1976_04
Patent number
US03950355

Reaction notes

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