Methanol → 1-(3-chloro-2-pyridinyl)-3-isopropyl-1H-pyrazole-5-carboxylic acid

HRID 251953Notes

Reaction equation

HRID 251953 reaction equation
[Cl:1][C:2]1[C:3]([N:8]2[C:12]([C:13]([O:15]CC)=[O:14])=[CH:11][C:10]([CH:18]([CH3:20])[CH3:19])=[N:9]2)=[N:4][CH:5]=[CH:6][CH:7]=1.CO.[OH-].[Na+]>O>[Cl:1][C:2]1[C:3]([N:8]2[C:12]([C:13]([OH:15])=[O:14])=[CH:11][C:10]([CH:18]([CH3:20])[CH3:19])=[N:9]2)=[N:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 66855071ethyl 1-(3-chloro-2-pyridinyl)-3-isopropyl-1H-pyrazole-5-carboxylate

Product 1

HCID 668543011-(3-chloro-2-pyridinyl)-3-isopropyl-1H-pyrazole-5-carboxylic acidYield 100.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 1.07 g of ethyl 1-(3-chloro-2-pyridinyl)-3-isopropyl-1H-pyrazole-5-carboxylate, 15 ml of methanol and 15 ml of a 2N aqueous sodium hydroxide solution was heated to reflux for 1.5 hours. After the reaction mixture was allowed to cool, water was poured and the mixture was washed with methyl t-butyl ether two times. The aqueous layer was adjusted to around pH 3 by an addition of 2N hydrochloric acid, and then extracted with methyl t-butyl ether three times. The combined organic layer was washed with an aqueous saturated sodium chloride solution, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to obtain 0.97 g of 1-(3-chloro-2-pyridinyl)-3-isopropyl-1H-pyrazole-5-carboxylic acid of the formula:

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 1.5 hours
  3. temperatureto cool
  4. washthe mixture was washed with methyl t-butyl ether two times
  5. additionThe aqueous layer was adjusted to around pH 3 by an addition of 2N hydrochloric acid
  6. extractionextracted with methyl t-butyl ether three times
  7. washThe combined organic layer was washed with an aqueous saturated sodium chloride solution
  8. dry with materialdried over anhydrous magnesium sulfate
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-321f575ec18647eba928236b4f16c87c
Source dataset
uspto-grants-2011_01
Patent number
US07867949B2

Reaction notes

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