Methanol → 5-Oxo-1-phenyl-4,5-dihydro-1H-[1,2,4]triazole-3-carboxylic Acid

HRID 541501Notes

Reaction equation

HRID 541501 reaction equation
[O:1]=[C:2]1[N:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[NH:5][C:4]([C:13]([O:15]C)=[O:14])=[N:3]1.CO.O>>[O:1]=[C:2]1[N:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[N:5]=[C:4]([C:13]([OH:15])=[O:14])[NH:3]1

Participants

4

Reactant 3

HCID 887MethanolHCID 962WaterHCID 178499135HCID 178499135, compound

Product 1

HCID 1354826545-Oxo-1-phenyl-4,5-dihydro-1H-[1,2,4]triazole-3-carboxylic AcidYield 64.4%

Procedure

Methyl 2,5-dihydro-5-oxo-1-phenyl-1h-1,2,4-triazole-3-carboxylate (300.0 mg, 1.4 mmol) was mixed with MeOH (4.5 mL, 110 mmol) and water (0.5 mL, 30 mmol) at room temperature, then treated with LiOH monohydrate (0.1 g, 2.7 mmol) at room temperature overnight. The mixture was concentrated and the resulting residue was acidified to pH˜1 with 1N aqueous HCl. The resulting solids were filtered and rinsed with water, then dried in vacuo to give the title compound as a yellowish solid (185 mg), which was used without further purification.

Workup

  1. concentrationThe mixture was concentrated
  2. filtrationThe resulting solids were filtered
  3. washrinsed with water
  4. customdried in vacuo

Sources & evidence

ORD record
ord-1e6df9d8afb1493c91b784161c9ae416
Source dataset
uspto-grants-2014_10
Patent number
US08871792B2

Reaction notes

Loading…