3-Nitrobenzaldehyde → HCID 54510285, compound

HRID 1197661Notes

Reaction equation

HRID 1197661 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([CH2:7][C:8](=[O:10])[CH3:9])=[CH:3][CH:2]=1.[N+:11]([C:14]1[CH:15]=[C:16]([CH:19]=[CH:20][CH:21]=1)[CH:17]=O)([O-:13])=[O:12].C([O-])(=O)C.[NH2+]1CCCCC1>C1C=CC=CC=1>[N+:11]([C:14]1[CH:15]=[C:16]([CH:17]=[C:7]([C:4]2[CH:5]=[CH:6][N:1]=[CH:2][CH:3]=2)[C:8](=[O:10])[CH3:9])[CH:19]=[CH:20][CH:21]=1)([O-:13])=[O:12]

Participants

5

Reactant 3

HCID 74493-NitrobenzaldehydeHCID 805524-PyridinylacetoneHCID 3014295Piperidinium acetate

Product 1

HCID 54510285HCID 54510285, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

4.62 g (34 mmole) of 1-(4-pyridyl)-2-propanone and 5.14 g (34 mmol) of 3-nitrobenzaldehyde were dissolved in benzene. To this solution, 0.49 g (3.4 mmol) of piperidinium acetate was added, and the mixture was refluxed with application of heat for 6 hours for dehydration. The reaction mixture was washed with water, and dried over anhydrous sodium sulfate. The benzene contained in the reaction mixture was distilled off under reduced pressure and the remaining reaction product was chromatographed on a silica gel column, whereby the captioned compound was obtained. The yield was 7.695 g (87.3%).

Workup

  1. temperaturethe mixture was refluxed with application
  2. temperatureof heat for 6 hours for dehydration
  3. washThe reaction mixture was washed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationwas distilled off under reduced pressure
  6. customthe remaining reaction product
  7. customwas chromatographed on a silica gel column, whereby the captioned compound
  8. customwas obtained

Sources & evidence

ORD record
ord-3830e8a8ca094c8093f1cf9791e37998
Source dataset
uspto-grants-1994_01
Patent number
US05276150

Reaction notes

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