3-Nitrobenzaldehyde → HCID 67289282, compound

HRID 2045217Notes

Reaction equation

HRID 2045217 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:14]=[C:15]([CH:18]=[CH:19][CH:20]=1)[CH:16]=O)([O-:12])=[O:11]>C(O)C>[N+:10]([C:13]1[CH:14]=[C:15]([CH:18]=[CH:19][CH:20]=1)[CH:16]=[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 74493-NitrobenzaldehydeHCID 133964-Aminobenzonitrile

Product 1

HCID 67289282HCID 67289282, compoundYield 83.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 4-amino-benzonitrile (11.8 g, 100 mmol) and 3-nitro-benzaldehyde (16.6 g, 110 mmol) in ethanol (100 mL) was prepared. The reaction mixture was heated to reflux for 3 h. Then the reaction mixture cooled to room temperature. The solvent was removed in vacuo and the residue was washed with ether to afford 4-[(3-nitro-benzylidene)-amino]-benzonitrile (21 g, 83%) as a white solid: LC/MS m/e calcd for C14H9N3O2 (M+H)+: 252.25, observed: 252.1.

Workup

  1. customwas prepared
  2. temperatureThe reaction mixture was heated
  3. temperatureto reflux for 3 h
  4. customThe solvent was removed in vacuo
  5. washthe residue was washed with ether

Sources & evidence

ORD record
ord-339cfef6df9047a78a7199f86b0eb732
Source dataset
uspto-grants-2013_11
Patent number
US08586747B2

Reaction notes

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