3-Nitrobenzaldehyde → N-(4-Chlorophenyl)-3-nitrobenzenemethanimine

HRID 1800932Notes

Reaction equation

HRID 1800932 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH2:8])=[CH:4][CH:3]=1.[N+:9]([C:12]1[CH:13]=[C:14]([CH:17]=[CH:18][CH:19]=1)[CH:15]=O)([O-:11])=[O:10]>C(O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]=[CH:15][C:14]2[CH:17]=[CH:18][CH:19]=[C:12]([N+:9]([O-:11])=[O:10])[CH:13]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 74493-NitrobenzaldehydeHCID 78124-Chloroaniline

Product 1

HCID 690813N-(4-Chlorophenyl)-3-nitrobenzenemethanimineYield 92.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 4-chloro-phenylamine (6.4 g, 50 mmol) and 3-nitro-benzaldehyde (8.31 g, 55 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-chloro-phenyl)-(3-nitro-benzylidene)-amine (12 g, 92%) as a light yellow oil: LC/MS m/e calcd for C13H9ClN2O2 (M+H)+: 261.68, observed: 261.0.

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-e4f8231d2f164f7bb64afb453833d6a1
Source dataset
uspto-grants-2013_01
Patent number
US08344137B2

Reaction notes

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