Sodium Hydroxide → 1-(4-Methoxyphenyl)pyrrole-3-carboxylic acid

HRID 1748487Notes

Reaction equation

HRID 1748487 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[CH:13]=[CH:12][C:11]([CH:14]=[O:15])=[CH:10]2)=[CH:5][CH:4]=1.[OH-].[Na+].[Mn]([O-])(=O)(=O)=[O:19].[K+]>N1C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([N:9]2[CH:13]=[CH:12][C:11]([C:14]([OH:19])=[O:15])=[CH:10]2)=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 516875Potassium PermanganateHCID 105599931-(4-methoxyphenyl)-1H-pyrrole-3-carbaldehyde

Product 1

HCID 685730691-(4-Methoxyphenyl)pyrrole-3-carboxylic acid

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Next, 1-(4-methoxyphenyl)pyrrole-3-carbaldehyde was added to an aqueous solution (100 ml) of sodium hydroxide (4.38 g) and an aqueous pyridine solution (water 100 ml and pyridine 180 ml) of potassium permanganate (8.65 g) at 20-30° C., and stirred at room temperature for six hours. After completion of the reaction, the reaction solution was filtered through Celite, the filtrate was acidified by the addition of hydrochloric acid and extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, concentrated in vacuo and the precipitated solid was purified with ethyl acetate/n-hexane to give the titled compound (8.52 g).

Workup

  1. customAfter completion of the reaction
  2. filtrationthe reaction solution was filtered through Celite
  3. additionthe filtrate was acidified by the addition of hydrochloric acid
  4. extractionextracted with ethyl acetate
  5. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  6. concentrationconcentrated in vacuo
  7. customthe precipitated solid was purified with ethyl acetate/n-hexane

Sources & evidence

ORD record
ord-3cd4ab85432045039c01e8401cd8225d
Source dataset
uspto-grants-2015_10
Patent number
US09150555B2

Reaction notes

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