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

HRID 1029405Notes

Reaction equation

HRID 1029405 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 1 N 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 1 N 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-dfd099da9ac04a1a9ac0ff71efe1744b
Source dataset
uspto-grants-1992_04
Patent number
US05102878

Reaction notes

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