4-Nitrobenzaldehyde → HCID 53735462, compound

HRID 728113Notes

Reaction equation

HRID 728113 reaction equation
[N+:1]([C:4]1[CH:11]=[CH:10][C:7]([CH:8]=O)=[CH:6][CH:5]=1)([O-:3])=[O:2].[N:12]1[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][C:13]=1[CH3:19]>C(OC(=O)C)(=O)C>[CH3:18][C:15]1[CH:16]=[CH:17][N:12]=[C:13]([CH:19]=[CH:8][C:7]2[CH:10]=[CH:11][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=2)[CH:14]=1

Participants

4

Reactant 2

HCID 5414-NitrobenzaldehydeHCID 79362,4-Dimethylpyridine

Product 1

HCID 53735462HCID 53735462, compoundYield 46%

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Procedure

A mixture of 4-nitrobenzaldehyde (30.2 g) and 2,4-lutidine (64.2 g) in acetic anhydride (100 ml) was refluxed for 11 hours under stirring. The reaction mixture was evaporated in vacuo and the residue was dissolved in a mixture of ethyl acetate and water. The resultant solution was acidified to pH 0.8 with conc. hydrochloric acid and the mixture was stirred at ambient temperature for one hour. The precipitate was collected by filtration. The residue was suspended in a mixture of ethyl acetate, tetrahydrofuran and water and the resultant mixture was adjusted to pH 8.0 with aqueous 20% potassium carbonate. The separated organic layer was washed with brine and dried over magnesium sulfate. The solvent was evaporated in vacuo and the residue was subjected to column chromatography on silica gel. The fraction eluted with a mixture of ethyl acetate and diisopropyl ether (4:6 V/V) was collected and the solvent was evaporated in vacuo to give 4-methyl-2-[2-(4-nitrophenyl)vinyl]pyridine (22.1 g).

Workup

  1. temperaturewas refluxed for 11 hours
  2. customThe reaction mixture was evaporated in vacuo
  3. dissolutionthe residue was dissolved in a mixture of ethyl acetate and water
  4. stirringthe mixture was stirred at ambient temperature for one hour
  5. filtrationThe precipitate was collected by filtration
  6. additionThe residue was suspended in a mixture of ethyl acetate, tetrahydrofuran and water
  7. washThe separated organic layer was washed with brine
  8. dry with materialdried over magnesium sulfate
  9. customThe solvent was evaporated in vacuo
  10. washThe fraction eluted with a mixture of ethyl acetate and diisopropyl ether (4:6 V/V)
  11. customwas collected
  12. customthe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-430154838b2e49e799a8df94c375d468
Source dataset
uspto-grants-1991_09
Patent number
US05047411

Reaction notes

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