Hydrochloric Acid → 1,4-Dimethyl-1H-pyrazole-3-carboxylic acid

HRID 244687

Reaction equation

HRID 244687 reaction equation
[OH-].[Li+].C1COCC1.[CH3:8][N:9]1[CH:13]=[C:12]([CH3:14])[C:11]([C:15]([O:17]C)=[O:16])=[N:10]1.Cl>O>[CH3:8][N:9]1[CH:13]=[C:12]([CH3:14])[C:11]([C:15]([OH:17])=[O:16])=[N:10]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 20718566methyl 1,4-dimethyl-1H-pyrazole-3-carboxylate

Product 1

HCID 53256851,4-Dimethyl-1H-pyrazole-3-carboxylic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Lithium hydroxide (0.864 g), THF (30 ml) and water (30 ml) were added to methyl 1,4-dimethyl-1H-pyrazole-3-carboxylate (1.39 g) and the reaction was stirred at room temperature for 3 h. The reaction was acidified with 5M HCl (aq) to pH to 7 and then washed through a waters HLB OASIS cation exchange cartridge. The cartridge was preconditioned with methanol, then water. The reaction was loaded onto the cartridge and washed with water, then eluted with methanol. The methanol fraction was evaporated in vacuo to give title compound, 1.1 g.

Workup

  1. washwashed through a waters HLB OASIS cation exchange cartridge
  2. washwashed with water
  3. washeluted with methanol
  4. customThe methanol fraction was evaporated in vacuo

Sources & evidence

ORD record
ord-96d268033c7b46709567f9bdc6904a32
Source dataset
uspto-grants-2014_02
Patent number
US08658635B2

Linked notes

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