Sulfuric Acid → HCID 20322007, compound

HRID 436807Notes

Reaction equation

HRID 436807 reaction equation
[CH3:1][N:2]([CH3:12])[C:3]1[CH:11]=[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][N:5]2[N:4]=1.S(=O)(=O)(O)O.C(=O)([O-])[O-].[K+].[K+].[C:24](OC(=O)C)(=[O:26])[CH3:25]>>[C:24]([C:11]1[C:3]([N:2]([CH3:12])[CH3:1])=[N:4][N:5]2[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=12)(=[O:26])[CH3:25]

Participants

5

Reactant 4

HCID 1118Sulfuric AcidHCID 7918Acetic AnhydrideHCID 11430Potassium CarbonateHCID 20322001HCID 20322001, compound

Product 1

HCID 20322007HCID 20322007, compound

Procedure

A mixture of 2.3g of 2-dimethylaminopyrazolo[1,5-a]pyridine and 30 ml of acetic anhydride in the presence of concentrated sulfuric acid was refluxed for 2.5 hr. After cooling, the mixture was poured into ice water. The solution was neutralized with potassium carbonate and extracted with chloroform. The chloroform solution was dried over sodium sulfate and concentrated. The residue was column chromatographed over alumina to purify the objective product. Recrystallization from n-hexane gave colorless prisms, mp 80.5°-81.5°. Yield 700 mg.

Workup

  1. temperaturewas refluxed for 2.5 hr
  2. temperatureAfter cooling
  3. extractionextracted with chloroform
  4. dry with materialThe chloroform solution was dried over sodium sulfate
  5. concentrationconcentrated
  6. customchromatographed over alumina
  7. customto purify the objective product
  8. customRecrystallization from n-hexane
  9. customgave colorless prisms, mp 80.5°-81.5°

Sources & evidence

ORD record
ord-8d594e6dfd8a49bd903b767200ce75f5
Source dataset
uspto-grants-1977_06
Patent number
US04028370

Reaction notes

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