Methanol → 1-methyl-1H-1,2,4-triazole-3-carboxylic acid

HRID 244638Notes

Reaction equation

HRID 244638 reaction equation
[CH3:1][N:2]1[CH:6]=[N:5][C:4]([C:7]([O:9]C)=[O:8])=[N:3]1.CO.[OH-].[K+]>O>[CH3:1][N:2]1[CH:6]=[N:5][C:4]([C:7]([OH:9])=[O:8])=[N:3]1

Participants

5

Reactant 3

HCID 887MethanolHCID 14797Potassium HydroxideHCID 19778899Methyl 1-methyl-1H-[1,2,4]triazole-3-carboxylate

Product 1

HCID 219818021-methyl-1H-1,2,4-triazole-3-carboxylic acidYield 71.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Methyl 1-methyl-1H-1,2,4-triazole-3-carboxylate (280 mg) and methanol (1 ml) were added to potassium hydroxide (145 mg) in water (1 ml). The reaction was stirred for 3 h at RT. The solvent was evaporated and the residue was loaded onto an aminopropyl SPE cartridge (5 g) in DMF. The cartridge was washed with 10% methanol in DCM (3×15 ml), followed by 30% acetic acid in methanol. The appropriate fractions were combined, the solvent was evaporated and the residue dried at 50° C. under vacuum to give title compound (180 mg).

Workup

  1. customThe solvent was evaporated
  2. washThe cartridge was washed with 10% methanol in DCM (3×15 ml)
  3. customthe solvent was evaporated
  4. customthe residue dried at 50° C. under vacuum

Sources & evidence

ORD record
ord-98df9ed834e444249769fe85d39b8089
Source dataset
uspto-grants-2014_02
Patent number
US08658635B2

Reaction notes

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