Hydrochloric Acid → HCID 68326506, compound

HRID 2274007Notes

Reaction equation

HRID 2274007 reaction equation
[Cl:1][C:2]1[C:3]([C:13]2([Cl:16])[CH2:15][CH2:14]2)=[N:4][N:5]([CH3:12])[C:6]=1[C:7]([O:9]CC)=[O:8].[OH-].[Na+].Cl>C(O)C>[Cl:1][C:2]1[C:3]([C:13]2([Cl:16])[CH2:14][CH2:15]2)=[N:4][N:5]([CH3:12])[C:6]=1[C:7]([OH:9])=[O:8]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 68326381HCID 68326381, compound

Product 1

HCID 68326506HCID 68326506, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

517 mg (1.76 mmol) of ethyl 4-chloro-3-(1-chlorocyclopropyl)-1-methyl-1H-pyrazole-5-carboxylate (purity 89%) are dissolved in 10 ml of ethanol p.a. 3.5 ml (3.5 mmol) of 1 N aqueous sodium hydroxide solution are then added to the solution, and the mixture is stirred at room temperature for 16 h. The reaction mixture is acidified by addition of 1 N hydrochloric acid. The aqueous phase is extracted twice with ethyl acetate. The combined organic phases are washed with saturated sodium chloride solution, dried over sodium sulphate and filtered. The solvent is removed under reduced pressure on a rotary evaporator. This gives 422 mg (99%) of 4-chloro-3-(1-chlorocyclopropyl)-1-methyl-1H-pyrazole-5-carboxylic acid.

Workup

  1. extractionThe aqueous phase is extracted twice with ethyl acetate
  2. washThe combined organic phases are washed with saturated sodium chloride solution
  3. dry with materialdried over sodium sulphate
  4. filtrationfiltered
  5. customThe solvent is removed under reduced pressure on a rotary evaporator

Sources & evidence

ORD record
ord-9fd1cf07367740cd8394d0d385973ee0
Source dataset
uspto-grants-2015_09
Patent number
US09126945B2

Reaction notes

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