Dimethylformamide → 1-(4-Fluorophenyl)pyrrole-3-carboxylic acid

HRID 1748493Notes

Reaction equation

HRID 1748493 reaction equation
CN(C)C=[O:4].[Mn]([O-])(=O)(=O)=O.[K+].[F:12][C:13]1[CH:18]=[CH:17][C:16]([N:19]2[CH:23]=[CH:22][C:21]([CH:24]=[O:25])=[CH:20]2)=[CH:15][CH:14]=1.[OH-].[Na+]>O>[F:12][C:13]1[CH:14]=[CH:15][C:16]([N:19]2[CH:23]=[CH:22][C:21]([C:24]([OH:4])=[O:25])=[CH:20]2)=[CH:17][CH:18]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 14798Sodium HydroxideHCID 516875Potassium Permanganate2×HCID 4715098HCID 4715098, compound

Product 1

HCID 222280401-(4-Fluorophenyl)pyrrole-3-carboxylic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

N,N-Dimethylformamide (300 ml) and water (100 ml) were added to potassium permanganate (28.7 g), and 1-(4-fluorophenyl)-3-formylpyrrole (34.4 g) was added under ice cooling. Potassium permanganate (14.4 g) was further added and the mixture was warmed up to room temperature and stirred for two hours. 1N Aqueous solution of sodium hydroxide (300 ml) was added to the reaction solution and stirred at room temperature for 0.5 hour. The reaction solution was washed with ethyl acetate, neutralized by the addition of hydrochloric acid and extracted with ethyl acetate. The organic layer was concentrated, isopropylether was added to the residue and the precipitated solid was collected by filtration to give the titled compound (15.2 g).

Workup

  1. additionwas added under ice cooling
  2. stirringstirred at room temperature for 0.5 hour
  3. washThe reaction solution was washed with ethyl acetate
  4. additionneutralized by the addition of hydrochloric acid
  5. extractionextracted with ethyl acetate
  6. concentrationThe organic layer was concentrated
  7. additionisopropylether was added to the residue
  8. filtrationthe precipitated solid was collected by filtration

Sources & evidence

ORD record
ord-04c318460bb743dab29de806494a6b17
Source dataset
uspto-grants-2015_10
Patent number
US09150555B2

Reaction notes

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