Piperidine → Ethyl 3-(1,2-dihydro-1-methyl-2-oxo-4-pyridinyl)-2-propenoate

HRID 1719533Notes

Reaction equation

HRID 1719533 reaction equation
[CH3:1][N:2]1[CH:7]=[CH:6][C:5]([CH:8]=O)=[CH:4][C:3]1=[O:10].[C:11]([O:17][CH2:18][CH3:19])(=[O:16])[CH2:12]C([O-])=O.N1CCCCC1>N1C=CC=CC=1>[CH3:1][N:2]1[CH:7]=[CH:6][C:5]([CH:8]=[CH:12][C:11]([O:17][CH2:18][CH3:19])=[O:16])=[CH:4][C:3]1=[O:10]

Participants

5

Reactant 3

HCID 8082PiperidineHCID 3595298Propanedioic acid, monoethyl esterHCID 142938901-Methyl-2-oxo-1,2-dihydropyridine-4-carbaldehyde

Product 1

HCID 53764784Ethyl 3-(1,2-dihydro-1-methyl-2-oxo-4-pyridinyl)-2-propenoate

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

N-Methyl-4-formyl-2-pyridone* (30.17 g), monoethyl malonate (38.15 g), pyridine (150 ml) and piperidine (3 ml) were stirred under reflux for 61/2 hours. The reaction mixture was evaporated under reduced pressure to afford a residue which was crystallised from aqueous isopropanol to give ethyl β-(N-methyl-2-oxo-4-pyridyl)acrylate as a pale yellow solid (18.44 g), m.p. 126°-7° C.

Workup

  1. temperatureunder reflux for 61/2 hours
  2. customThe reaction mixture was evaporated under reduced pressure
  3. customto afford a residue which
  4. customwas crystallised from aqueous isopropanol

Sources & evidence

ORD record
ord-ade9dd96662e495abdc2f1c14f53e4af
Source dataset
uspto-grants-1985_09
Patent number
US04540699

Reaction notes

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