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

HRID 1744486Notes

Reaction equation

HRID 1744486 reaction equation
[Mn]([O-])(=O)(=O)=O.[K+].[OH-].[Na+].CN(C)C=[O:12].[F:14][C:15]1[CH:20]=[CH:19][C:18]([N:21]2[CH:25]=[CH:24][C:23]([CH:26]=[O:27])=[CH:22]2)=[CH:17][CH:16]=1>N1C=CC=CC=1>[F:14][C:15]1[CH:16]=[CH:17][C:18]([N:21]2[CH:25]=[CH:24][C:23]([C:26]([OH:12])=[O:27])=[CH:22]2)=[CH:19][CH:20]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 14798Sodium HydroxideHCID 516875Potassium PermanganateHCID 4715098HCID 4715098, compound

Product 1

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

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Potassium permanganate (13 g) and sodium hydroxide (6.6 g) were added to a solution of dimethylformamide (150 ml) and pyridine (130 ml), and 1-(4-fluorophenyl)-3-formylpyrrole (30 g) was added thereto under ice-cooling with stirring. The mixture was warmed to room temperature and stirred further for 3 h. The reaction mixture was filtrated and the filtrate was neutralized with hydrochloric acid. The precipitated crystals were recrystallized from hydrous ethanol to give 1-(4-fluorophenyl)pyrrole-3-carboxylic acid (9.2 g), melting point 204–205° C.

Workup

  1. additionwas added
  2. temperatureunder ice-cooling
  3. stirringstirred further for 3 h
  4. filtrationThe reaction mixture was filtrated
  5. customThe precipitated crystals were recrystallized from hydrous ethanol

Sources & evidence

ORD record
ord-759ee2a7b1df4864a436f8126b3da22f
Source dataset
uspto-grants-2006_03
Patent number
US07015218B1

Reaction notes

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