HCID 53693258, compound → HCID 53923255, compound

HRID 1650751Notes

Reaction equation

HRID 1650751 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 53693258HCID 53693258, compound

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 IN 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-91dbd4f7a65a46b0834e9020ce3dd9b3
Source dataset
uspto-grants-1990_05
Patent number
US04925849

Reaction notes

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