Methyl 3-(2-phenylpyrazolo[1,5-a]pyridin-3-yl)acrylate → HCID 53923255, compound

HRID 1029421Notes

Reaction equation

HRID 1029421 reaction equation
[C:1]1([C:7]2[C:15]([CH:16]=[CH:17][C:18]([O:20]C)=[O:19])=[C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][N:9]3[N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>[OH-].[Na+].CO>[C:1]1([C:7]2[C:15]([CH:16]=[CH:17][C:18]([OH:20])=[O:19])=[C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][N:9]3[N:8]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 1

HCID 53693258Methyl 3-(2-phenylpyrazolo[1,5-a]pyridin-3-yl)acrylate

Product 1

HCID 53923255HCID 53923255, compoundYield 68.9%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

A mixture of methyl 3-(2-phenylpyrazolo[1,5-a]pyridin-3-yl)acrylate (trans isomer) (4.05 g) in 1N sodium hydroxide solution (58.3 ml) and methanol (80 ml) was refluxed for 1 hour and evaporated in vacuo. The residue was dissolved in water and washed with chloroform. The aqueous layer was acidified with 1N hydrochloric acid. The resulting precipitates were filtered and recrystallized from isopropyl alcohol to give crystals of 3-(2-phenylpyrazolo[1,5-a]-pyridin-3-yl)acrylic acid (2.65 g).

Workup

  1. temperaturewas refluxed for 1 hour
  2. customevaporated in vacuo
  3. dissolutionThe residue was dissolved in water
  4. washwashed with chloroform
  5. customThe resulting precipitates
  6. filtrationwere filtered
  7. customrecrystallized from isopropyl alcohol

Sources & evidence

ORD record
ord-07940946ea9947d9bc768ea27116a4a1
Source dataset
uspto-grants-1992_04
Patent number
US05102869

Reaction notes

Loading…