Methanol → 2-Methylpyrazolo[1,5-a]pyridine-3-carboxylic acid

HRID 1589834Notes

Reaction equation

HRID 1589834 reaction equation
CO.[CH3:3][C:4]1[C:12]([C:13]([O:15]CC)=[O:14])=[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][N:6]2[N:5]=1>[OH-].[Na+]>[CH3:3][C:4]1[C:12]([C:13]([OH:15])=[O:14])=[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][N:6]2[N:5]=1

Participants

4

Reactant 2

HCID 887MethanolHCID 12872285Ethyl 2-methylpyrazolo[1,5-a]pyridine-3-carboxylate

Product 1

HCID 128722962-Methylpyrazolo[1,5-a]pyridine-3-carboxylic acidYield 52.4%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

A small amount of methanol was added to a solution of 0.356 g of ethyl 2-methyl-3-pyrazolo[1,5-a]-pyridinecarboxylate in 10 ml of 5N aq. NaOH solution, followed by stirring at room temperature for 24 hours. The reaction mixture was washed with benzene and then made acidic with concentrated hydrochloric acid. Crystals precipitated were collected by suction filtration. The crystals so obtained were dried and then recrystallized from benzene, whereby 0.16 g of the title compound was obtained (yield: 52.4%).

Workup

  1. washThe reaction mixture was washed with benzene
  2. customCrystals precipitated
  3. filtrationwere collected by suction filtration
  4. customThe crystals so obtained
  5. customwere dried
  6. customrecrystallized from benzene

Sources & evidence

ORD record
ord-ffa7cb32f58540528db749a437ea17ad
Source dataset
uspto-grants-1993_04
Patent number
US05200415

Reaction notes

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