Dimethylformamide → 1-(4-fluorophenyl)-1H-pyrrole-2-carboxylic acid

HRID 1744484Notes

Reaction equation

HRID 1744484 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][CH:23]=[C:22]2[CH:26]=[O:27])=[CH:17][CH:16]=1>N1C=CC=CC=1>[F:14][C:15]1[CH:20]=[CH:19][C:18]([N:21]2[CH:25]=[CH:24][CH:23]=[C:22]2[C:26]([OH:12])=[O:27])=[CH:17][CH:16]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 14798Sodium HydroxideHCID 516875Potassium PermanganateHCID 31618451-(4-fluorophenyl)-1H-pyrrole-2-carbaldehyde

Product 1

HCID 173900441-(4-fluorophenyl)-1H-pyrrole-2-carboxylic acid

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Potassium permanganate (30.1 g) and sodium hydroxide (15.3 g) were added to a solution of dimethylformamide (380 ml) and pyridine (300 ml), and 1-(4-fluorophenyl)-2-formylpyrrole (30 g) was further 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-2-carboxylic acid (20 g), melting point 195–196° C.

Workup

  1. additionwas further 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-ea1cf8740bc14519945b7a3c43b22e48
Source dataset
uspto-grants-2006_03
Patent number
US07015218B1

Reaction notes

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