2-Nitrobenzaldehyde → 5312-49-2

HRID 1036891Notes

Reaction equation

HRID 1036891 reaction equation
[NH2:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=1.[N+:10]([C:13]1[CH:20]=[CH:19][CH:18]=[CH:17][C:14]=1[CH:15]=O)([O-:12])=[O:11]>C(O)C>[N+:10]([C:13]1[CH:20]=[CH:19][CH:18]=[CH:17][C:14]=1[CH:15]=[N:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=1)([O-:12])=[O:11]

Participants

4

Reactant 2

HCID 111012-NitrobenzaldehydeHCID 133964-Aminobenzonitrile

Product 1

HCID 6164635312-49-2Yield 79.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The mixture of 4-aminobenzonitrile (20 g, 0.17 mol) and 2-nitrobenzaldehyde (28.2 g, 0.17 mol) in anhydrous ethanol was heated to reflux for 3 h. The reaction mixture was cooled to room temperature. The solvent was removed under reduced pressure. The residue was washed with diethyl ether to give 4-(2-nitrobenzylideneamino)benzonitrile as yellow solid (33.7 g, yield 79.3%) LC/MS m/e obsd. (ESI+) [(M+H)+] 252.10.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 3 h
  3. customThe solvent was removed under reduced pressure
  4. washThe residue was washed with diethyl ether

Sources & evidence

ORD record
ord-4e7a7291dd9c4b8c98ba6eb171ccb03d
Source dataset
uspto-grants-2013_10
Patent number
US08546427B2

Reaction notes

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