Hydrochloric Acid → Zomepirac

HRID 1585610Notes

Reaction equation

HRID 1585610 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-(p-chlorobenzoyl)-1,4 -dimethylpyrrole-2-acetate in 26 ml. of 0.5 N sodium hydroxide (0.013 mole) is heated under reflux for 30 minutes. The resulting solutions is acidified with dilute hydrochloric acid, and the precipitated solid is collected by filtration, air dried and recrystallized from 2-propanol to give 5-(p-chlorobenzoyl)-1,4-dimethylpyrrole-2-acetic acid as a white crystalline solid, m.p. 178-179° C. Anal. Calcd. for C15H14ClNO3 : C, 61.76; H, 4.83; N, 4.82%. Found: C, 61.68; H, 4.96; N, 4.89%.

Workup

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

Sources & evidence

ORD record
ord-4d9ff6fe45b44d9e83199010edf507e6
Source dataset
uspto-grants-1999_08
Patent number
US05939417

Reaction notes

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