Sodium Hydroxide → 1-methyl-1H-1,2,3-triazole-5-carboxylic acid

HRID 1094799Notes

Reaction equation

HRID 1094799 reaction equation
[CH3:1][N:2]1[C:6]([CH:7]=[O:8])=[CH:5][N:4]=[N:3]1.[OH-].[Na+].[Mn]([O-])(=O)(=O)=[O:12].[K+]>O>[CH3:1][N:2]1[C:6]([C:7]([OH:12])=[O:8])=[CH:5][N:4]=[N:3]1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 516875Potassium PermanganateHCID 211875071-Methyl-1H-1,2,3-triazole-5-carbaldehyde

Product 1

HCID 205771431-methyl-1H-1,2,3-triazole-5-carboxylic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

To a solution of 1-methyl-1H-1,2,3-triazole-5-carbaldehyde (Preparation 33, 5 g, 45 mmol) and sodium hydroxide (8.59 g, 215 mmol) in water (120 ml) at 15° C. was added dropwise a solution of potassium permanganate (5.83 g, 36.9 mmol) in water (120 ml). The reaction was stirred at room temperature for 30 minutes and then heated to reflux for 1 hour. The reaction was filtered and the filtrate acidified to pH 3 with concentrated HCl before extracting with ethyl acetate (3×100 ml). The combined organic extracts were washed with saturated aqueous brine, dried over Na2SO4 and concentrated in vacuo to afford the title compound.

Workup

  1. temperatureheated
  2. temperatureto reflux for 1 hour
  3. filtrationThe reaction was filtered
  4. extractionbefore extracting with ethyl acetate (3×100 ml)
  5. washThe combined organic extracts were washed with saturated aqueous brine
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-73a70a38c7384a2fbac89c9ab3660e9d
Source dataset
uspto-grants-2012_03
Patent number
US08134007B2

Reaction notes

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