Potassium Hydroxide → 2-Isopropylpyrazolo[1,5-a]pyridine-3-carboxylic acid

HRID 731734Notes

Reaction equation

HRID 731734 reaction equation
[CH:1]([C:4]1[C:12]([CH:13]=[O:14])=[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][N:6]2[N:5]=1)([CH3:3])[CH3:2].[Mn]([O-])(=O)(=O)=[O:16].[K+].[OH-].[K+]>C1COCC1.O>[CH:1]([C:4]1[C:12]([C:13]([OH:16])=[O:14])=[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][N:6]2[N:5]=1)([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 14797Potassium HydroxideHCID 516875Potassium PermanganateHCID 143032672-Isopropylpyrazolo[1,5-a]pyridine-3-carbaldehyde

Product 1

HCID 578374592-Isopropylpyrazolo[1,5-a]pyridine-3-carboxylic acidYield 60.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 2-isopropylpyrazolo[1,5-a]pyridine-3-carbaldehyde (1.5 g, 1 equivalent) and potassium permanganate (2.9 g, 2.1 equivalents) in 10 mL of THF was stirred at room temperature for 2 days. A solution of potassium hydroxide (2.2 g, 5 equivalents) in 10 mL of water was added and the resulting solution was stirred at room temperature for 2 hours. The mixture was filtered to remove insoluble solids and the filtrate was extracted to remove unreacted aldehyde. The remaining aqueous solution was acidified with concentrated HCl and the precipitates were collected by filtration and dried under reduced pressure to give 2-isopropylpyrazolo[1,5-a]pyridine-3-carboxylic acid (0.98 g, 60% yield) as a solid. Compound 1079.

Workup

  1. stirringthe resulting solution was stirred at room temperature for 2 hours
  2. filtrationThe mixture was filtered
  3. customto remove insoluble solids
  4. extractionthe filtrate was extracted
  5. customto remove unreacted aldehyde
  6. filtrationthe precipitates were collected by filtration
  7. customdried under reduced pressure

Sources & evidence

ORD record
ord-11e85c5f963f4f1b97409560ea22af2f
Source dataset
uspto-grants-2009_09
Patent number
US07585875B2

Reaction notes

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