219761-99-6 → HCID 22388192, compound

HRID 1072782Notes

Reaction equation

HRID 1072782 reaction equation
[CH3:1][C:2]1[CH:13]=[C:5]2[CH:6]=[C:7]([C:10]([OH:12])=[O:11])[CH:8]=[CH:9][N:4]2[N:3]=1.S(=O)(=O)(O)O.[CH2:19](O)[CH3:20]>>[CH3:1][C:2]1[CH:13]=[C:5]2[CH:6]=[C:7]([C:10]([O:12][CH2:19][CH3:20])=[O:11])[CH:8]=[CH:9][N:4]2[N:3]=1

Participants

3

Reactant 2

HCID 22388435219761-99-6HCID 73950302Sulphuric acid ethanol

Product 1

HCID 22388192HCID 22388192, compound

Procedure

2-Methylpyrazolo[1,5-a]pyridine-5-carboxylic acid (723 mg) was dissolved in 10% sulfuric acid/ethanol (20 ml) and the mixture was refluxed under heating for 2.5 hr. The reaction mixture was neutralized under ice-cooling, extracted with ethyl acetate and dried over magnesium sulfate. The residue was concentrated to dryness under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=4:1) to give the objective compound (707 mg) as a pale-brown powder.

Workup

  1. temperaturethe mixture was refluxed
  2. temperatureunder heating for 2.5 hr
  3. temperaturecooling
  4. extractionextracted with ethyl acetate
  5. dry with materialdried over magnesium sulfate
  6. concentrationThe residue was concentrated to dryness under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=4:1)

Sources & evidence

ORD record
ord-b5955b54c40544ae8431a35eb0b9074c
Source dataset
uspto-grants-2005_06
Patent number
US06911469B2

Reaction notes

Loading…