Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Ammonia | HCID 222 | — |
| Reactant | Malonic Acid | HCID 867 | — |
| Reactant | Piperidine | HCID 8082 | — |
| Reactant | HCID 20267137 | HCID 20267137 | — |
| Solvent | Acetic Acid | HCID 176 | — |
| Solvent | Acetone | HCID 180 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Pyridine | HCID 1049 | — |
| Product | HCID 53857067 | HCID 53857067 | 73.2% |
Reaction Steps
N-n-Butyl-4-formyl-2-pyridone (68.71 g), malonic acid (39.90 g), pyridine (225 ml) and piperidine (4.5 ml) were stirred under reflux for 6 hours. The reaction mixture was evaporated under reduced pressure to afford an oil, to which was added water and a small amount of ammonia ('880 solution) to aid dissolution. The solution was taken to pH 4 with acetic acid, the solvent volume was diminished under reduced pressure and acetone added to precipitate a solid. After cooling at 0° C. for a few hours the solid was collected by filtration, washed with acetone and dried in vacuo to afford β-(N-n-butyl-2-oxo-4-pyridyl)acrylic acid (62.06 g) as a white solid, m.p. 131°-134° C.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US04540699 |
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| Source dataset | uspto-grants-1985_09 |
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| ORD ID | ord-66ee77556beb47708a91fa1580df85f4 |
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| Source note | uspto-grants-1985_09 |
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