Potassium Hydroxide → 5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxylic Acid
Reaction equation
C([O:3][C:4]([C:6]1[C:10]([CH3:11])=[C:9]([CH:12]=[O:13])[NH:8][C:7]=1[CH3:14])=[O:5])C.[OH-].[K+]>CO>[CH:12]([C:9]1[NH:8][C:7]([CH3:14])=[C:6]([C:4]([OH:5])=[O:3])[C:10]=1[CH3:11])=[O:13]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 65 °C
Procedure
Into a 10-L four necked round-bottomed flask equipped with a mechanical stirrer, a thermometer pocket, addition funnel and reflux condenser were charged 5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxylic acid ethyl ester (IV) (0.6 Kg; 3.09 mole), methanol (2.0 L) and aqueous KOH solution (prepared by dissolving 450 g KOH in 1.8 L of water), stirred well and raised the reaction mass temperature to 60-70° C. and maintained for 4-6 hours. The progress of the reaction was monitored by TLC. After completion of the reaction, the excess solvent was removed under diminished pressure and the resulting product was diluted with water and extracted with ethylacetate. The aqueous layer was separated and the pH adjusted to 4.0 with conc. HCl. The resulting solution was stirred over night at 25-30° C. The product was filtered and washed with water. The product was dried at 60° C.
Workup
- additiona thermometer pocket, addition funnel
- temperaturereflux condenser
- temperaturemaintained for 4-6 hours
- customAfter completion of the reaction
- customthe excess solvent was removed under diminished pressure
- additionthe resulting product was diluted with water
- extractionextracted with ethylacetate
- customThe aqueous layer was separated
- stirringThe resulting solution was stirred over night at 25-30° C
- filtrationThe product was filtered
- washwashed with water
- customThe product was dried at 60° C.
Sources & evidence
- ORD record
- ord-a0265f6edfee48d98ad9476bb09e138a
- Source dataset
- uspto-grants-2013_08
- Patent number
- US08501962B2
Reaction notes
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