4-(Trifluoromethyl)aniline → N-(2-nitrobenzylidene)-4-(trifluoromethyl)aniline

HRID 1036919Notes

Reaction equation

HRID 1036919 reaction equation
[F:1][C:2]([F:11])([F:10])[C:3]1[CH:9]=[CH:8][C:6]([NH2:7])=[CH:5][CH:4]=1.[N+:12]([C:15]1[CH:22]=[CH:21][CH:20]=[CH:19][C:16]=1[CH:17]=O)([O-:14])=[O:13]>C(O)C>[N+:12]([C:15]1[CH:22]=[CH:21][CH:20]=[CH:19][C:16]=1[CH:17]=[N:7][C:6]1[CH:8]=[CH:9][C:3]([C:2]([F:10])([F:11])[F:1])=[CH:4][CH:5]=1)([O-:14])=[O:13]

Participants

4

Reactant 2

HCID 99644-(Trifluoromethyl)anilineHCID 111012-Nitrobenzaldehyde

Product 1

HCID 67291521N-(2-nitrobenzylidene)-4-(trifluoromethyl)anilineYield 72.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 4-(trifluoromethyl)aniline (5 g) and 2-nitrobenzaldehyde (5.2 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 N-(2-nitrobenzylidene)-4-(trifluoromethyl)aniline as yellow solid (6.6 g, yield 72.3%). LC/MS m/e obsd. (ESI+) [(M+H)+] 295.1.

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-9b5314839bd44cbea1cd720abece30ba
Source dataset
uspto-grants-2013_10
Patent number
US08546427B2

Reaction notes

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