Sulfuric Acid → HCID 20322007, compound

HRID 839795Notes

Reaction equation

HRID 839795 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-4b0bb25a364a4b62ab7f72cf7f95aaae
Source dataset
uspto-grants-1978_06
Patent number
US04097483

Reaction notes

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