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

HRID 1411137Notes

Reaction equation

HRID 1411137 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 66.6%

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 concentrated to dryness under high vacuum, treated with water (300 mL) and washed with EtOAc (2×250 mL) to remove the impurities. The pH of the aqueous was adjusted with NaHCO3 to pH ˜9-10. The mixture was extracted with DCM (3×300 mL). The combined organics were washed with brine, dried over Na2SO4 and concentrated. The residue was purified by silica gel chromatography to afford ethyl 4-ethoxy-2-oxo-1,2-dihydropyridine-3-carboxylate (90 g, 66.6% yield).

Workup

  1. temperaturewas refluxed overnight
  2. concentrationThe mixture was concentrated to dryness under high vacuum
  3. additiontreated with water (300 mL)
  4. washwashed with EtOAc (2×250 mL)
  5. customto remove the impurities
  6. extractionThe mixture was extracted with DCM (3×300 mL)
  7. washThe combined organics were washed with brine
  8. dry with materialdried over Na2SO4
  9. concentrationconcentrated
  10. customThe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-c9c9722257894ef09fe35b5b4ba3bde4
Source dataset
uspto-grants-2014_12
Patent number
US08921565B2

Reaction notes

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