Hydrochloric Acid → 5-Methylpyrazolo[1,5-a]pyridine-3-carboxylic acid

HRID 931024Notes

Reaction equation

[CH3:1][C:2]1[CH:7]=[CH:6][N:5]2[N:8]=[CH:9][C:10]([C:11]([O:13]CC)=[O:12])=[C:4]2[CH:3]=1.[OH-].[Na+].Cl>C1COCC1.CCO>[CH3:1][C:2]1[CH:7]=[CH:6][N:5]2[N:8]=[CH:9][C:10]([C:11]([OH:13])=[O:12])=[C:4]2[CH:3]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of ethyl 5-methylpyrazolo[1,5-a]pyridine-3-carboxylate (2.73 g) in THF/EtOH (30/15 mL) was added 1N aqueous sodium hydroxide solution (20 mL), and the mixture was stirred at 80° C. for 4 hr. To the reaction mixture was added 1N hydrochloric acid at 0° C., and the mixture was extracted with THF/EtOAc. The extract was washed with saturated brine, and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was washed with cooled hexane/IPE to give the title compound (2.11 g).

Workup

extractionthe mixture was extracted with THF/EtOAc
washThe extract was washed with saturated brine
dry with materialdried over anhydrous sodium sulfate
customthe solvent was evaporated under reduced pressure
washThe residue was washed with cooled hexane/IPE

Sources & evidence

ORD record: ord-990ffdf512f040119163ed0bc3fa89c5
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09296746B2

Reaction notes

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