Hydrochloric Acid → Zomepirac

HRID 863629Notes

Reaction equation

HRID 863629 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.[OH-].[Na+].Cl>>[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

4

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 118463ethyl 5-(4-chlorobenzoyl)-1,4-dimethyl-1H-pyrrole-2-acetate

Product 1

HCID 5733Zomepirac

Procedure

A suspension of 4.0 g. (0.0125 mole) of ethyl 5-(ρ-chlorobenzoyl)-1,4-dimethylpyrrole-2-acetate in 26 ml. of 0.5N sodium hydroxide (0.013 mole) is heated under reflux for 30 mins. The resulting solution is acidified with dilute hydrochloric acid, and the precipitated solid is collected by filtration, air dried and recrystallized from 2-propanol to give 5-(ρ-chlorobenzoyl)-1,4-dimethylpyrrole-2-acetic acid as a white crystalline solid, M.P. 178°-179° C.

Workup

  1. additionA suspension of 4.0 g
  2. temperatureunder reflux for 30 mins
  3. filtrationthe precipitated solid is collected by filtration, air
  4. customdried
  5. customrecrystallized from 2-propanol

Sources & evidence

ORD record
ord-1faeb14a371f465aa23a0e9ee7575d2f
Source dataset
uspto-grants-1998_02
Patent number
US05721347

Reaction notes

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