Hydrochloric Acid → 1-(2-Methylphenyl)-1H-1,2,4-triazole-3-carboxylic acid

HRID 1755220Notes

Reaction equation

HRID 1755220 reaction equation
[C:1]1([CH3:17])[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[N:7]1[CH:11]=[N:10][C:9]([C:12]([O:14]CC)=[O:13])=[N:8]1.[Li+].[OH-].CO.Cl>C1COCC1>[C:1]1([CH3:17])[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[N:7]1[CH:11]=[N:10][C:9]([C:12]([OH:14])=[O:13])=[N:8]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 3939Lithium HydroxideHCID 71304241Ethyl 1-(2-methylphenyl)-1H-1,2,4-triazole-3-carboxylate

Product 1

HCID 713020931-(2-Methylphenyl)-1H-1,2,4-triazole-3-carboxylic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of ethyl 1-(o-tolyl)-1,2,4-triazole-3-carboxylate (400 mg, 1.7 mmol) in 3 mL THF was added 4 M LiOH (2 mL, 8 mmol) followed by 3 mL of MeOH. The reaction mixture was stirred at 50° C. for 5 minutes, after which the pH was adjusted to 4 with the addition of conc. HCl. After extraction, drying (MgSO4), filtration and drying under reduced pressure, 43 mg of residue was recovered (12%) and used in the subsequent step without further purification.

Workup

  1. extractionAfter extraction
  2. customdrying
  3. filtration(MgSO4), filtration
  4. dry with materialdrying under reduced pressure, 43 mg of residue
  5. customwas recovered (12%)
  6. customused in the subsequent step without further purification

Sources & evidence

ORD record
ord-17a51cb946f349c5b0cc40a8e4901319
Source dataset
uspto-grants-2015_10
Patent number
US09169261B2

Reaction notes

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