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

HRID 1606179Notes

Reaction equation

HRID 1606179 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 min. The solution is filtered while hot and acidified with dilute hydrochloric acid. The precipitate is collected, air dried and recrystallised 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 min
  3. filtrationThe solution is filtered while hot and
  4. customThe precipitate is collected
  5. customair dried
  6. customrecrystallised from 2-propanol
  7. customto give about 2.5 g

Sources & evidence

ORD record
ord-28580c4a2b21472491596be4f64f9586
Source dataset
uspto-grants-1976_04
Patent number
US03952012

Reaction notes

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