4-Nitrobenzaldehyde → p-Nitrocinnamonitrile

HRID 863419Notes

Reaction equation

HRID 863419 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 H2 O. 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 H2 O
  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-bc4fbfee85b94a5fa1628b3df22d0373
Source dataset
uspto-grants-1998_02
Patent number
US05721240

Reaction notes

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