Acetic Acid → Ethyl 4-Ethoxy-2-oxo-1,2-dihydropyridine-3-carboxylate

HRID 1472602Notes

Reaction equation

HRID 1472602 reaction equation
C([C:3](=[C:9]([O:15][CH2:16][CH3:17])[CH:10]=[CH:11][N:12](C)[CH3:13])[C:4]([O:6][CH2:7][CH3:8])=[O:5])#N.CC(O)=[O:20]>>[CH2:16]([O:15][C:9]1[CH:10]=[CH:11][NH:12][C:13](=[O:20])[C:3]=1[C:4]([O:6][CH2:7][CH3:8])=[O:5])[CH3:17]

Participants

3

Reactant 2

HCID 176Acetic AcidHCID 54113151Ethyl 2-cyano-5-(dimethylamino)-3-ethoxypenta-2,4-dienoate

Product 1

HCID 53393185Ethyl 4-Ethoxy-2-oxo-1,2-dihydropyridine-3-carboxylateYield 67%

Procedure

A mixture of ethyl 2-cyano-5-(dimethylamino)-3-ethoxypenta-2,4-dienoate (150 g, 0.63 mol) and HOAc (600 mL) was refluxed overnight. The mixture was cooled to RT, concentrated to dryness, treated with water and washed with EtOAc (2×). The aqueous layer was made basic (pH=9-10) with NaHCO3, extracted with DCM (3×) and the combined organics were washed with brine, dried over Na2SO4, concentrated and purified by silica gel chromatography to afford ethyl 4-ethoxy-2-oxo-1,2-dihydropyridine-3-carboxylate (90 g, 67% yield).

Workup

  1. temperaturewas refluxed overnight
  2. concentrationconcentrated to dryness
  3. additiontreated with water
  4. washwashed with EtOAc (2×)
  5. extractionextracted with DCM (3×)
  6. washthe combined organics were washed with brine
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated
  9. custompurified by silica gel chromatography

Sources & evidence

ORD record
ord-7995408463434641a6e69e2c29b4eff2
Source dataset
uspto-grants-2015_04
Patent number
US09012635B2

Reaction notes

Loading…