Acetic Acid → HCID 54018731, compound

HRID 2351943Notes

Reaction equation

HRID 2351943 reaction equation
[N+:1]([C:4]1[CH:11]=[CH:10][CH:9]=[CH:8][C:5]=1[CH:6]=O)([O-:3])=[O:2].[CH:12]([NH:15][C:16](=[O:21])[CH2:17][C:18]([CH3:20])=[O:19])([CH3:14])[CH3:13].N1CCCCC1.C(O)(=O)C>C1C=CC=CC=1>[CH:12]([NH:15][C:16](=[O:21])[CH2:17][C:18]([CH:20]=[CH:6][C:5]1[CH:8]=[CH:9][CH:10]=[CH:11][C:4]=1[N+:1]([O-:3])=[O:2])=[O:19])([CH3:14])[CH3:13]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 8082PiperidineHCID 111012-NitrobenzaldehydeHCID 957140HCID 957140, compound

Product 1

HCID 54018731HCID 54018731, compoundYield 78.4%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

o-Nitrobenzaldehyde (43.4 g, 0.29 mole) and acetoacetic isopropylamide (40.0 g, 0.29 mole) are dissolved in benzene (150 ml) and thereto are added piperidine (1.15 ml) and acetic acid (3.45 ml), and the mixture is refluxed and the produced water is removed. After the stoichiometic amount of water is distilled off, the reaction is stopped. After the reaction, the solvent is distilled off under reduced pressure, and the residue is recrystallized from ethanol to give the title compound (62.7 g, yield 78.4%) as colorless prisms, m.p. 132°-135° C.

Workup

  1. temperaturethe mixture is refluxed
  2. customthe produced water is removed
  3. distillationAfter the stoichiometic amount of water is distilled off
  4. customAfter the reaction
  5. distillationthe solvent is distilled off under reduced pressure
  6. customthe residue is recrystallized from ethanol

Sources & evidence

ORD record
ord-d3b94c45dd20425ab4d25de0c145b192
Source dataset
uspto-grants-1989_10
Patent number
US04874773

Reaction notes

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