Sodium Hydroxide → Zomepirac

HRID 1154992Notes

Reaction equation

HRID 1154992 reaction equation
[Cl:1][C:2]1[CH:20]=[CH:19][C:5]([C:6]([C:8]2[N:12]([CH3:13])[C:11]([CH2:14][C:15]([O-:17])=[O:16])=[CH:10][C:9]=2[CH3:18])=[O:7])=[CH:4][CH:3]=1.[OH-].[Na+]>>[CH3:18][C:9]1[CH:10]=[C:11]([CH2:14][C:15]([OH:17])=[O:16])[N:12]([CH3:13])[C:8]=1[C:6]([C:5]1[CH:4]=[CH:3][C:2]([Cl:1])=[CH:20][CH:19]=1)=[O:7]

Participants

3

Reactant 2

HCID 14798Sodium HydroxideHCID 69218215-(p-Chlorobenzoyl)-1,4-dimethylpyrrole-2-acetate

Product 1

HCID 5733ZomepiracYield 86%

Procedure

About 31 grams of the lower alkyl ester form of 5-(p-chlorobenzoyl)-1,4-dimethylpyrrole-2-acetate are saponified in 225 ml. of an aqueous reaction medium containing 0.12 M.NaOH. Saponification is carried out at about 90° C. for a period of from about 2 to 4 hours. At the end of this period, the aqueous saponification medium is cooled to a temperature of 0° to 5° C. The resulting insoluble first crop of acetate salt product is removed from the aqueous mother liquor. An 86-88% yield of Zomepirac [sodium 5-(p-chlorobenzoyl)-1,4 -dimethylpyrrole-2-acetate] is thereby realized based on the amount of ester initially employed.

Workup

  1. additionof an aqueous reaction medium containing 0.12 M
  2. temperatureAt the end of this period, the aqueous saponification medium is cooled to a temperature of 0° to 5° C
  3. customThe resulting insoluble first crop of acetate salt product is removed from the aqueous mother liquor

Sources & evidence

ORD record
ord-f5dc6f5b31384a8fa2ef3eaf996cbeb5
Source dataset
uspto-grants-1981_11
Patent number
US04299770

Reaction notes

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