Sodium Hydroxide → Pyrazolo(1,5-a)pyridine-3-carboxylic acid

HRID 1500754Notes

Reaction equation

HRID 1500754 reaction equation
[OH-].[Na+].[N:3]1[N:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]2=[C:5]([C:12]([O:14]CC)=[O:13])[CH:4]=1>C(O)C>[N:3]1[N:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]2=[C:5]([C:12]([OH:14])=[O:13])[CH:4]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 2795464Ethyl pyrazolo(1,5-a)pyridine-3-carboxylate

Product 1

HCID 2795462Pyrazolo(1,5-a)pyridine-3-carboxylic acidYield 77%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A 2.5 N aqueous solution of sodium hydroxide (36 mL) was added to a solution of ethyl pyrazolo[1,5-a]pyridine-3-carboxylate (Preparation 22a, 4.3 g, 22.6 mmol) in ethanol (70 mL) and the resulting reaction mixture was heated to reflux for 1 h. After evaporation of the ethanol, the reaction mixture was acidified with 15% aqueous hydrochloric acid solution. The solid formed was filtered, washed with water and diethyl ether and dried to give the title compound (2.81 g, 77%) as a pale pink solid.

Workup

  1. customthe resulting reaction mixture
  2. temperaturewas heated
  3. temperatureto reflux for 1 h
  4. customAfter evaporation of the ethanol
  5. customThe solid formed
  6. filtrationwas filtered
  7. washwashed with water and diethyl ether
  8. customdried

Sources & evidence

ORD record
ord-67497fcd245142cc8d6a9400f04a64da
Source dataset
uspto-grants-2015_12
Patent number
US09206183B2

Reaction notes

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