Hydrochloric Acid → HCID 135973146, compound

HRID 70897Notes

Reaction equation

HRID 70897 reaction equation
[O:1]=[C:2]1[O:6][N:5]=[C:4]([C:7]([O:9]CC)=[O:8])[NH:3]1.[OH-].[Na+].Cl>CO>[O:1]=[C:2]1[O:6][N:5]=[C:4]([C:7]([OH:9])=[O:8])[NH:3]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 135973140Ethyl 5-hydroxy-1,2,4-oxadiazole-3-carboxylate

Product 1

HCID 135973146HCID 135973146, compoundYield 96.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of crude ethyl 5-oxo-4,5-dihydro-1,2,4-oxadiazole-3-carboxylate (2.4 g, 15.14 mmol) in MeOH (2 mL) is added aqueous 1N NaOH (4 mL, 4 mmol) at room temperature. After stirring for 5 hours at room temperature the reaction is quenched with 1N HCl (5 mL, 5 mmol), the crude is concentrated under reduced pressure to remove MeOH. The crude is diluted with EtOAc, the organic layer is washed with brine, dried over Na2SO4, filtered and concentrated under reduced pressure to give 5-oxo-4,5-dihydro-1,2,4-oxadiazole-3-carboxylic acid (1.9 g).

Workup

  1. concentrationthe crude is concentrated under reduced pressure
  2. customto remove MeOH
  3. additionThe crude is diluted with EtOAc
  4. washthe organic layer is washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-c0372e2e1f194ca99ddbd94233d4244d
Source dataset
uspto-grants-2014_09
Patent number
US08822534B2

Reaction notes

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