Water → Methyl 5-(3-methyl-1,2,4-oxadiazol-5-yl)-3-pyridinecarboxylate

HRID 399799

Reaction equation

HRID 399799 reaction equation
S(Cl)(Cl)=O.[CH3:5][C:6]1[N:10]=[C:9]([C:11]2[CH:12]=[C:13]([C:17]([OH:19])=[O:18])[CH:14]=[N:15][CH:16]=2)[O:8][N:7]=1.[C:20](OCC)(=O)C.O>CO>[CH3:5][C:6]1[N:10]=[C:9]([C:11]2[CH:12]=[C:13]([C:17]([O:19][CH3:20])=[O:18])[CH:14]=[N:15][CH:16]=2)[O:8][N:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 24386Thionyl ChlorideHCID 189454415-(3-Methyl-1,2,4-oxadiazol-5-yl)-3-pyridinecarboxylic acid

Product 1

HCID 18945172Methyl 5-(3-methyl-1,2,4-oxadiazol-5-yl)-3-pyridinecarboxylate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Thionyl chloride (2.5 ml) was added dropwise in methanol (25 ml) under cooling at 7°-9° C. After the mixture was stirred for 30 minutes at the same temperature, 5-(3-methyl-1,2,4-oxadiazol-5-yl)-3-pyridinecarboxylic acid (2.5 g) was added thereto and the mixture was refluxed for 3 hours. After being cooled to room temperature, the mixture was poured into a mixture of ethyl acetate (100 ml) and water (100 ml). The organic layer was successively washed with 10% potassium carbonate aqueous solution and brine, and then dried over magnesium sulfate. The solvent was evaporated in vacuo and the residue was recrystallized from diethyl ether to afford methyl 5-(3-methyl-1,2,4-oxadiazol-5-yl)-3-pyridinecarboxylate (2.12 g).

Workup

  1. temperatureunder cooling at 7°-9° C
  2. additionwas added
  3. temperaturethe mixture was refluxed for 3 hours
  4. washThe organic layer was successively washed with 10% potassium carbonate aqueous solution and brine
  5. dry with materialdried over magnesium sulfate
  6. customThe solvent was evaporated in vacuo
  7. customthe residue was recrystallized from diethyl ether

Sources & evidence

ORD record
ord-c530c3da336340a2a690ddab9eb9c047
Source dataset
uspto-grants-1998_10
Patent number
US05824691

Linked notes

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