4-Nitrobenzaldehyde → p-Nitrocinnamonitrile

HRID 864985Notes

Reaction equation

HRID 864985 reaction equation
[C:1]([CH2:3]C(O)=O)#[N:2].[N+:7]([C:10]1[CH:17]=[CH:16][C:13]([CH:14]=O)=[CH:12][CH:11]=1)([O-:9])=[O:8].C([O-])(=O)C.[NH4+].C1(C)C=CC=CC=1>N1C=CC=CC=1>[N+:7]([C:10]1[CH:17]=[CH:16][C:13]([CH:14]=[CH:3][C:1]#[N:2])=[CH:12][CH:11]=1)([O-:9])=[O:8]

Participants

6

Reactant 4

HCID 5414-NitrobenzaldehydeHCID 1140TolueneHCID 9740Cyanoacetic acidHCID 517165Ammonium Acetate

Product 1

HCID 34056p-Nitrocinnamonitrile

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of cyanoacetic acid (12.76 g, 150.0 mmol), 4-nitrobenzaldehyde (24.60 g, 162.8 mmol), ammonium acetate (500 mg), toluene (140 mL), and pyridine (75 mL) is refluxed for 64 hours in a flask fitted with a Dean-Stark trap and condenser. After evaporation of the solvents, a solution of the residue in CHCl3 is filtered and washed with H2O. The dried (Na2SO4) organic layer is evaporated, and the bright yellow-orange solid is recrystallized from benzene. The yellow solid 3-(4-nitrophenyl)-acrylonitrile, obtained as a mixture of cis-trans isomers, is suitable for use as an intermediate without further purification.

Workup

  1. temperatureis refluxed for 64 hours in a flask
  2. customfitted with a Dean-Stark trap and condenser
  3. customAfter evaporation of the solvents
  4. filtrationa solution of the residue in CHCl3 is filtered
  5. washwashed with H2O
  6. dry with materialThe dried (Na2SO4) organic layer
  7. customis evaporated
  8. customthe bright yellow-orange solid is recrystallized from benzene

Sources & evidence

ORD record
ord-242772f6ed89491ea96852220a5ebb3f
Source dataset
uspto-grants-1996_10
Patent number
US05565463

Reaction notes

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