3-Nitrobenzaldehyde → HCID 67850751, compound

HRID 1197660Notes

Reaction equation

HRID 1197660 reaction equation
N1C=CC=C[C:2]=1[CH2:7][C:8](=[O:10])[CH3:9].[N+:11]([C:14]1[CH:15]=[C:16]([CH:19]=[CH:20][CH:21]=1)C=O)([O-:13])=[O:12].C([O-])(=O)C.[NH2+:26]1[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]1>C1C=CC=CC=1>[N+:11]([C:14]1[CH:21]=[C:20]([C:29]2[CH:30]=[CH:31][N:26]=[CH:27][C:28]=2[CH2:9][C:8](=[O:10])[CH:7]=[CH2:2])[CH:19]=[CH:16][CH:15]=1)([O-:13])=[O:12]

Participants

5

Reactant 3

HCID 74493-NitrobenzaldehydeHCID 959101-(Pyridin-2-yl)propan-2-oneHCID 3014295Piperidinium acetate

Product 1

HCID 67850751HCID 67850751, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

2.76 g (20 mmol) of 1-pyridyl-2-propanone and 3.066 g (20 mmol) of 3-nitrobenzaldehyde were dissolved in benzene. To this solution, 0.29 g (2.0 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 4.5 g (87.9%).

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-7a7d8bf34d844e46b3bb094cbf77405d
Source dataset
uspto-grants-1994_01
Patent number
US05276150

Reaction notes

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