Ammonia → HCID 53857067, compound

HRID 1719538Notes

Reaction equation

HRID 1719538 reaction equation
[CH2:1]([N:5]1[CH:10]=[CH:9][C:8]([CH:11]=O)=[CH:7][C:6]1=[O:13])[CH2:2][CH2:3][CH3:4].C(O)(=O)[CH2:15][C:16]([OH:18])=[O:17].N1CCCCC1.N>CC(C)=O.C(O)(=O)C.O.N1C=CC=CC=1>[CH2:1]([N:5]1[CH:10]=[CH:9][C:8]([CH:11]=[CH:15][C:16]([OH:18])=[O:17])=[CH:7][C:6]1=[O:13])[CH2:2][CH2:3][CH3:4]

Participants

9

Reactant 4

HCID 222AmmoniaHCID 867Malonic AcidHCID 8082PiperidineHCID 20267137HCID 20267137, compound

Product 1

HCID 53857067HCID 53857067, compoundYield 73.2%

Reagents, catalysts & solvents 4

HCID 176Acetic AcidSolventHCID 180AcetoneSolventHCID 962WaterSolventHCID 1049PyridineSolvent

Conditions

Temperature
0 °C

Procedure

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.

Workup

  1. temperatureunder reflux for 6 hours
  2. customThe reaction mixture was evaporated under reduced pressure
  3. customto afford an oil
  4. dissolutiondissolution
  5. additionadded
  6. customto precipitate a solid
  7. filtrationwas collected by filtration
  8. washwashed with acetone
  9. customdried in vacuo

Sources & evidence

ORD record
ord-66ee77556beb47708a91fa1580df85f4
Source dataset
uspto-grants-1985_09
Patent number
US04540699

Reaction notes

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