Hydrochloric Acid → 2-(4-methyl-1H-1,2,3-triazol-1-yl)acetic acid

HRID 887157Notes

Reaction equation

HRID 887157 reaction equation
C([O:3][C:4](=[O:12])[CH2:5][N:6]1[CH:10]=[C:9]([CH3:11])[N:8]=[N:7]1)C.CO.[OH-].[Li+].Cl>O1CCCC1>[CH3:11][C:9]1[N:8]=[N:7][N:6]([CH2:5][C:4]([OH:12])=[O:3])[CH:10]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 3939Lithium HydroxideHCID 59603650Ethyl 4-methyl-1H-1,2,3-triazole-1-acetate

Product 1

HCID 185244432-(4-methyl-1H-1,2,3-triazol-1-yl)acetic acidYield 95%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 0.51 g (3.0 mmol) of ethyl [4-methyl-1H-1,2,3-triazole-1-yl]acetate from step B above in tetrahydrofuran (10 ml), methanol (6 ml) was added 6 mL (6 mmol) of an aqueous 1.0 M lithium hydroxide solution. The resulting mixture was stirred at ambient temperature for 1 h. The reaction mixture was neutralized with 8 mL of a 2 N hydrochloric acid solution which was then evaporated to remove all volatiles. The aqueous phase was extracted with ethyl acetate and the combined organics were washed with brine, dried over magnesium sulfate, filtered and evaporated to dryness to afford the title compound as a white solid (0.40 g, 95%). LC/MS 142 (M+1).

Workup

  1. customwas then evaporated
  2. customto remove all volatiles
  3. extractionThe aqueous phase was extracted with ethyl acetate
  4. washthe combined organics were washed with brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. customevaporated to dryness

Sources & evidence

ORD record
ord-d916b0d149fe4902b14b554eac15eb2a
Source dataset
uspto-grants-2012_08
Patent number
US08247415B2

Reaction notes

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