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

HRID 1282369Notes

Reaction equation

HRID 1282369 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-e2b2495adc7f4e25a5ad40e940376a48
Source dataset
uspto-grants-2002_09
Patent number
US06455703B2

Reaction notes

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