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

HRID 1646241Notes

Reaction equation

HRID 1646241 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-d6aff5801a874cc38566f84bc9ffab6b
Source dataset
uspto-grants-1993_01
Patent number
US05179103

Reaction notes

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