Hydrochloric Acid → 4-formyl-3,5-dimethyl-1H-pyrrole-2-carboxylic acid

HRID 553240Notes

Reaction equation

HRID 553240 reaction equation
C([O:3][C:4]([C:6]1[NH:7][C:8]([CH3:14])=[C:9]([CH:12]=[O:13])[C:10]=1[CH3:11])=[O:5])C.[OH-].[Na+].O.Cl>C(O)C>[CH3:11][C:10]1[C:9]([CH:12]=[O:13])=[C:8]([CH3:14])[NH:7][C:6]=1[C:4]([OH:5])=[O:3]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 1374862199-64-6

Product 1

HCID 6878984-formyl-3,5-dimethyl-1H-pyrrole-2-carboxylic acidYield 97%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

3,5-Dimethyl-4-formylpyrrole-2-carboxylic acid ethyl ester (19.52 g, 100 mmol) reported in the references was suspended in ethanol (100 ml) and a 2 N sodium hydroxide aqueous solution (100 ml, 200 mmol), and then stirred for 4 hours under reflux condition. After the completion of the reaction, 200 ml of water and 100 ml of a 2 N hydrochloric acid aqueous solution were added under the ice cooled. The precipitate was collected by filtration, washed with water and diethylether, and dried at reduced pressure to afford 3,5-dimethyl-4-formylpyrrole-2-carboxylic acid (16.18 g, 97%) as a light brown solid.

Workup

  1. temperatureunder reflux condition
  2. temperaturecooled
  3. filtrationThe precipitate was collected by filtration
  4. washwashed with water and diethylether
  5. customdried at reduced pressure

Sources & evidence

ORD record
ord-08176ddc3dc24b03a7cd7815b997ec55
Source dataset
uspto-grants-2011_05
Patent number
US07951956B2

Reaction notes

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