HCID 20242528, compound → HCID 54462082, compound

HRID 483092Notes

Reaction equation

HRID 483092 reaction equation
[CH:1]([C:4]1[C:12]([CH:13](O)[CH2:14][CH3:15])=[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][N:6]2[N:5]=1)([CH3:3])[CH3:2]>C(OC(=O)C)(=O)C>[CH:1]([C:4]1[C:12]([CH:13]=[CH:14][CH3:15])=[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][N:6]2[N:5]=1)([CH3:3])[CH3:2]

Participants

3

Reactant 1

HCID 20242528HCID 20242528, compound

Product 1

HCID 54462082HCID 54462082, compoundYield 78.5%

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Procedure

Five grams of 2-isopropyl-3-(1-hydroxypropyl)pyrazolo[1,5-a]pyridine (Example 8) were dissolved in 50 ml of acetic anhydride. The mixture was heated to reflux for 4 hours and concentrated to dryness. Water was added to the residue. The mixture was brought to alkaline by the addition of potassium carbonate and extracted with dichloromethane. The organic layer was dried over anhydrous sodium sulfate and concentrated to dryness. The residue was subjected to silica gel column chromatography, eluted with ethyl acetate-benzene (1:4) to give 3.6 g of the desired compound as pale yellow oil.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 4 hours
  3. concentrationconcentrated to dryness
  4. additionWater was added to the residue
  5. additionThe mixture was brought to alkaline by the addition of potassium carbonate
  6. extractionextracted with dichloromethane
  7. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  8. concentrationconcentrated to dryness
  9. washeluted with ethyl acetate-benzene (1:4)

Sources & evidence

ORD record
ord-4413b32877e54d5f8e813d12c0b3e32c
Source dataset
uspto-grants-1986_03
Patent number
US04578392

Reaction notes

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