Sodium Hydroxide → 4-methyl-1-(4-methylbenzyl)-3-p-tolyl-1H-pyrrole-2-carboxylic acid

HRID 2427409Notes

Reaction equation

HRID 2427409 reaction equation
C([O:3][C:4]([C:6]1[N:7]([CH2:19][C:20]2[CH:25]=[CH:24][C:23]([CH3:26])=[CH:22][CH:21]=2)[CH:8]=[C:9]([CH3:18])[C:10]=1[C:11]1[CH:16]=[CH:15][C:14]([CH3:17])=[CH:13][CH:12]=1)=[O:5])C.[OH-].[Na+]>CO.O>[CH3:18][C:9]1[C:10]([C:11]2[CH:12]=[CH:13][C:14]([CH3:17])=[CH:15][CH:16]=2)=[C:6]([C:4]([OH:5])=[O:3])[N:7]([CH2:19][C:20]2[CH:21]=[CH:22][C:23]([CH3:26])=[CH:24][CH:25]=2)[CH:8]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 671473774-Methyl-1-(4-methylbenzyl)-3-p-tolyl-1H-pyrrole-2-carboxylic acid ethyl ester

Product 1

HCID 668828154-methyl-1-(4-methylbenzyl)-3-p-tolyl-1H-pyrrole-2-carboxylic acid

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A reaction mixture of 4-methyl-1-(4-methylbenzyl)-3-p-tolyl-1H-pyrrole-2-carboxylic acid ethyl ester (550 mg, 1.58 mmol) and NaOH (1.26 g, 32 mmol) in MeOH (45 mL) and H2O (15 mL) was refluxed for 1 h. After removal of the solvent, aqueous 1N NaOH (100 mL) was added and extraction performed with EtOAc (2×20 mL). After drying of the combined organic phases over Na2SO4, filtration and removal of the solvent, the desired product 4-methyl-1-(4-methylbenzyl)-3-p-tolyl-1H-pyrrole-2-carboxylic acid was obtained, which was used without further purification.

Workup

  1. temperaturewas refluxed for 1 h
  2. customAfter removal of the solvent, aqueous 1N NaOH (100 mL)
  3. additionwas added
  4. extractionextraction
  5. dry with materialAfter drying of the combined organic phases over Na2SO4, filtration and removal of the solvent

Sources & evidence

ORD record
ord-0adde4b805de4cabac5fbe407ef6c809
Source dataset
uspto-grants-2011_06
Patent number
US07968591B2

Reaction notes

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