Sodium Hydroxide → 1H-Pyrrole-3-carboxylic acid, 1,2-dimethyl-5-phenyl-

HRID 339721Notes

Reaction equation

HRID 339721 reaction equation
C([C:3]1[C:4]([C:16]([OH:18])=[O:17])=[C:5]([CH3:15])[N:6]([CH3:14])[C:7]=1[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)C.[OH-].[Na+]>CCO>[CH3:14][N:6]1[C:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[CH:3][C:4]([C:16]([OH:18])=[O:17])=[C:5]1[CH3:15]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 67319812HCID 67319812, compound

Product 1

HCID 8529041H-Pyrrole-3-carboxylic acid, 1,2-dimethyl-5-phenyl-Yield 95%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To the solution of Ethyl 1,2-dimethyl-5-phenyl-1H-pyrrole-3-carboxylic acid (3 g, 13 mmol) in EtOH (50 ml) was added NaOH (1.6 g, 39 mmol) at room temperature. The reaction mixture was refluxed for 1 day with LC-MS monitoring. After reaction complete, EtOH was evaporated under reduced pressure. Water (50 ml) was added and washed aqueous layer with diethyl ether twice. 1N HCl solution was added to aqueous layer until pH<3. And extraction was accomplished with EtOAc. Organic layer was dried with MgSO4 and evaporated in vacuo to provide title compound (2.6 g, 95%) as yellow soild. Without further purification, acid was used for the reaction of amide coupling.

Workup

  1. temperatureThe reaction mixture was refluxed for 1 day with LC-MS monitoring
  2. customAfter reaction complete
  3. customEtOH was evaporated under reduced pressure
  4. additionWater (50 ml) was added
  5. washwashed aqueous layer with diethyl ether twice
  6. addition1N HCl solution was added to aqueous layer until pH<3
  7. extractionAnd extraction
  8. dry with materialOrganic layer was dried with MgSO4
  9. customevaporated in vacuo

Sources & evidence

ORD record
ord-a945c4de596f42bdbfceb1d570626adf
Source dataset
uspto-grants-2014_11
Patent number
US08895558B2

Reaction notes

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