Water → 5-methyl-3-(pyridin-4-yl)-1H-pyrazole-4-carboxylic acid

HRID 539674Notes

Reaction equation

HRID 539674 reaction equation
[CH3:1][C:2]1[NH:6][N:5]=[C:4]([C:7]2[CH:12]=[CH:11][N:10]=[CH:9][CH:8]=2)[C:3]=1[C:13]([O:15]CC)=[O:14].[OH-].[Na+].O>C(O)C>[CH3:1][C:2]1[NH:6][N:5]=[C:4]([C:7]2[CH:8]=[CH:9][N:10]=[CH:11][CH:12]=2)[C:3]=1[C:13]([OH:15])=[O:14]

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 67314713HCID 67314713, compound

Product 1

HCID 835320935-methyl-3-(pyridin-4-yl)-1H-pyrazole-4-carboxylic acidYield 88.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of ethyl 5-methyl-3-(pyridin-4-yl)-1H-pyrazole-4-carboxylate (3.1 g) in ethanol (20 mL) were added sodium hydroxide (8.0 g) and water (10 mL), and the mixture was heated under reflux overnight. The solvent was evaporated under reduced pressure, the pH of the mixture was adjusted to 5 with 2 N hydrochloric acid, and mixture was concentrated under reduced pressure. The obtained solid was collected by filtration and washed with water to give the title compound (2.4 g).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux overnight
  3. customThe solvent was evaporated under reduced pressure
  4. concentrationwas concentrated under reduced pressure
  5. filtrationThe obtained solid was collected by filtration
  6. washwashed with water

Sources & evidence

ORD record
ord-86226a465c304d5a8724097833627826
Source dataset
uspto-grants-2014_10
Patent number
US08871766B2

Reaction notes

Loading…