Acetyl chloride → Ethyl 2-oxo-1,2-dihydropyridine-4-carboxylate

HRID 500535Notes

Reaction equation

HRID 500535 reaction equation
[C:1](Cl)(=[O:3])[CH3:2].[OH:5][C:6]1[CH:11]=[C:10]([C:12](O)=[O:13])[CH:9]=[CH:8][N:7]=1>C(O)C>[CH2:1]([O:3][C:12]([C:10]1[CH:9]=[CH:8][NH:7][C:6](=[O:5])[CH:11]=1)=[O:13])[CH3:2]

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 178524562HCID 178524562, compound

Product 1

HCID 22625086Ethyl 2-oxo-1,2-dihydropyridine-4-carboxylateYield 96%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Acetyl chloride (20 mL) was added slowly to ethanol (80 mL) at room temperature. The clear solution was stirred for 5 minutes and then 2-hydroxy-4-pyridinecarboxylic acid (5.0 g, 35.9 mmol) was added as a solid. The reaction mixture was heated at reflux overnight. The reaction mixture was cooled to room temperature and the majority of the ethanol was evaporated. The residue was diluted with chloroform and water and the aqueous layer was neutralized by the careful addition of K2CO3. The organic layer was separated and the aqueous layer was extracted further with chloroform. The combined organic layer was dried over sodium sulfate and concentrated to give the title compound (5.74 g, 96%).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux overnight
  3. customthe majority of the ethanol was evaporated
  4. additionThe residue was diluted with chloroform and water
  5. additionthe aqueous layer was neutralized by the careful addition of K2CO3
  6. customThe organic layer was separated
  7. extractionthe aqueous layer was extracted further with chloroform
  8. dry with materialThe combined organic layer was dried over sodium sulfate
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-df0492600fc6478aa95dd6a0cd3d3479
Source dataset
uspto-grants-2010_08
Patent number
US07772235B2

Reaction notes

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