Ethyl Acetate → Methyl 5-(3-dimethylamino-1-oxo-2-propenyl)-3-pyridinecarboxylate

HRID 399797Notes

Reaction equation

HRID 399797 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]([C:10]([O:12][CH3:13])=[O:11])[CH:7]=[N:8][CH:9]=1)(=[O:3])[CH3:2].CO[CH:16](OC)[N:17]([CH3:19])[CH3:18].C(OCC)(=O)C>O1CCCC1>[CH3:16][N:17]([CH3:19])[CH:18]=[CH:2][C:1]([C:4]1[CH:5]=[C:6]([C:10]([O:12][CH3:13])=[O:11])[CH:7]=[N:8][CH:9]=1)=[O:3]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 78373Dimethylformamide dimethyl acetalHCID 596459Methyl 5-acetylpyridine-3-carboxylate

Product 1

HCID 53719482Methyl 5-(3-dimethylamino-1-oxo-2-propenyl)-3-pyridinecarboxylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

The mixture of methyl 5-acetyl-3-pyridinecarboxylate (3.0 g) and N,N-dimethylformamide dimethyl acetal (6.7 ml) in tetrahydrofuran (30 ml) was heated under reflux for 6 hours. To the mixture was added a mixture of ethyl acetate and tetrahydrofuran, and the mixture was washed with brine and dried over magnesium sulfate. The solvent was removed by concentration and the residue was triturated with diisopropyl ether to give methyl 5-(3-dimethylamino-1-oxo-2-propenyl)-3-pyridinecarboxylate (1.88 g).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 6 hours
  3. additionTo the mixture was added
  4. washthe mixture was washed with brine
  5. dry with materialdried over magnesium sulfate
  6. customThe solvent was removed by concentration
  7. customthe residue was triturated with diisopropyl ether

Sources & evidence

ORD record
ord-487d246417384e9d8383960f13b201dc
Source dataset
uspto-grants-1998_10
Patent number
US05824691

Reaction notes

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