p-Nitroacetophenone → HCID 3918365, compound

HRID 2176004Notes

Reaction equation

HRID 2176004 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10](=[O:12])[CH3:11])=[CH:6][CH:5]=1)([O-:3])=[O:2].[CH:13]([C:15]1[CH:24]=[CH:23][C:18]([C:19]([O:21][CH3:22])=[O:20])=[CH:17][CH:16]=1)=O.N1CCCCC1>C(O)C>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([C:10](=[O:12])[CH:11]=[CH:13][C:15]2[CH:24]=[CH:23][C:18]([C:19]([O:21][CH3:22])=[O:20])=[CH:17][CH:16]=2)=[CH:8][CH:9]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 7487p-NitroacetophenoneHCID 8082PiperidineHCID 15294Methyl 4-Formylbenzoate

Product 1

HCID 3918365HCID 3918365, compoundYield 77.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To a mixture of 16.5 g of 1-(4-nitrophenyl)ethanone, 16.4 g of methyl 4-formylbenzoate and 100 mL of ethanol was added dropwise 4.0 mL of piperidine at room temperature, followed by heating under reflux for 8 hours. The precipitate was collected by filtration, thereby obtaining 24.6 g of a crude product. The crude product was suspended in 100 mL of ethanol, followed by heating under reflux for 6 hours. The precipitate was collected by filtration, thereby obtaining 24.0 g of methyl 4-[3-(4-nitrophenyl)-3-oxoprop-1-en-1-yl]benzoate.

Workup

  1. temperatureby heating
  2. temperatureunder reflux for 8 hours
  3. filtrationThe precipitate was collected by filtration
  4. customobtaining 24.6 g of a crude product
  5. temperatureby heating
  6. temperatureunder reflux for 6 hours
  7. filtrationThe precipitate was collected by filtration

Sources & evidence

ORD record
ord-c5c37b32f8c34b8185c5a540df9596f1
Source dataset
uspto-grants-2015_06
Patent number
US09062032B2

Reaction notes

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