p-Toluidine → N-(2-Nitrobenzylidene)-P-toluidine

HRID 1036930Notes

Reaction equation

HRID 1036930 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][CH:3]=1.[N+:9]([C:12]1[CH:19]=[CH:18][CH:17]=[CH:16][C:13]=1[CH:14]=O)([O-:11])=[O:10]>C(O)C>[CH3:8][C:5]1[CH:6]=[CH:7][C:2]([N:1]=[CH:14][C:13]2[CH:16]=[CH:17][CH:18]=[CH:19][C:12]=2[N+:9]([O-:11])=[O:10])=[CH:3][CH:4]=1

Participants

4

Reactant 2

HCID 7813p-ToluidineHCID 111012-Nitrobenzaldehyde

Product 1

HCID 794913N-(2-Nitrobenzylidene)-P-toluidineYield 77.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The mixture of p-toluidine (10 g) and 2-nitrobenzaldehyde (14.1 g) 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 and petro ether to give 4-methyl-N-(2-nitrobenzylidene)aniline as yellow solid (17.3 g, yield 77.2%). LC/MS m/e obsd. (ESI+) [(M+H)+] 241.2.

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 and petro ether

Sources & evidence

ORD record
ord-ee99c622e4014617bc302cfe8c55c605
Source dataset
uspto-grants-2013_10
Patent number
US08546427B2

Reaction notes

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