Sodium Hydroxide → 1,4-Dimethyl-5-(p-fluorobenzoyl)-pyrrole-2-acetic acid

HRID 1275302Notes

Reaction equation

HRID 1275302 reaction equation
[CH3:1][N:2]1[C:6]([C:7](=[O:15])[C:8]2[CH:13]=[CH:12][C:11]([F:14])=[CH:10][CH:9]=2)=[C:5]([CH3:16])[CH:4]=[C:3]1[CH2:17][C:18]([O:20]CC)=[O:19].[OH-].[Na+]>>[CH3:1][N:2]1[C:6]([C:7](=[O:15])[C:8]2[CH:9]=[CH:10][C:11]([F:14])=[CH:12][CH:13]=2)=[C:5]([CH3:16])[CH:4]=[C:3]1[CH2:17][C:18]([OH:20])=[O:19]

Participants

3

Reactant 2

HCID 14798Sodium HydroxideHCID 18424154HCID 18424154, compound

Product 1

HCID 185443041,4-Dimethyl-5-(p-fluorobenzoyl)-pyrrole-2-acetic acidYield 91%

Procedure

A suspension of 3.03 g. (0.01 mole) of ethyl 1,4-dimethyl-5-(p-fluorobenzoyl)-pyrrole-2-acetate in 11 ml. of 1N sodium hyroxide solution is heated under reflux for 30 minutes. The solution is filtered while hot and acidified with dilute hydrochloric acid. The precipitate is collected, air dried and recrystallized from 2-propanol to give about 2.5 g. (91% yield) of 1,4-dimethyl-5-(p-fluorobenzoyl)-pyrrole-2-acetic acid as a white solid, m.p. 176-178° C.

Workup

  1. additionA suspension of 3.03 g
  2. temperatureunder reflux for 30 minutes
  3. filtrationThe solution is filtered while hot and
  4. customThe precipitate is collected
  5. customair dried
  6. customrecrystallized from 2-propanol
  7. customto give about 2.5 g

Sources & evidence

ORD record
ord-cab148371f7643388c38b6445885a65b
Source dataset
uspto-grants-2000_12
Patent number
US06160003

Reaction notes

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