Potassium Carbonate → 2-Isopropylpyrazolo[1,5-a]pyridine-3-carbaldehyde

HRID 436806Notes

Reaction equation

HRID 436806 reaction equation
[CH:1]([C:4]1[CH:12]=[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][N:6]2[N:5]=1)([CH3:3])[CH3:2].P(Cl)(Cl)(Cl)=O.[C:18](=O)([O-])[O-:19].[K+].[K+]>CN(C)C=O>[CH:18]([C:12]1[C:4]([CH:1]([CH3:3])[CH3:2])=[N:5][N:6]2[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=12)=[O:19]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 24813Phosphorus oxychlorideHCID 113786582-Isopropylpyrazolo[1,5-a]pyridine

Product 1

HCID 143032672-Isopropylpyrazolo[1,5-a]pyridine-3-carbaldehydeYield 67%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

One gram of 2-isopropylpyrazolo[1,5-a]pyridine was dissolved in 0.6 ml of dimethylformamide, and 5 ml of phosphorus oxychloride was added to the resulting solution. The reaction mixture was refluxed for 20 min., poured into ice-water, and neutralized with potassium carbonate. The precipitate was collected by filtration and washed with water. Recrystallization from n-hexane gave 800 mg of colorless needles, mp 81.0°-81.5°. Yield 67%.

Workup

  1. temperatureThe reaction mixture was refluxed for 20 min.
  2. filtrationThe precipitate was collected by filtration
  3. washwashed with water
  4. customRecrystallization from n-hexane

Sources & evidence

ORD record
ord-84c430faa55849acab8fad25f007299a
Source dataset
uspto-grants-1977_06
Patent number
US04028370

Reaction notes

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