3-Nitrobenzaldehyde → HCID 67291037, compound

HRID 2045237Notes

Reaction equation

HRID 2045237 reaction equation
[F:1][C:2]([F:11])([F:10])[C:3]1[CH:8]=[CH:7][C:6]([NH2:9])=[CH:5][CH:4]=1.[N+:12]([C:15]1[CH:16]=[C:17]([CH:20]=[CH:21][CH:22]=1)[CH:18]=O)([O-:14])=[O:13]>C(O)C>[N+:12]([C:15]1[CH:16]=[C:17]([CH:20]=[CH:21][CH:22]=1)[CH:18]=[N:9][C:6]1[CH:5]=[CH:4][C:3]([C:2]([F:10])([F:11])[F:1])=[CH:8][CH:7]=1)([O-:14])=[O:13]

Participants

4

Reactant 2

HCID 74493-NitrobenzaldehydeHCID 99644-(Trifluoromethyl)aniline

Product 1

HCID 67291037HCID 67291037, compoundYield 95.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 4-trifluoromethyl-phenylamine (2.6 mL, 21 mmol) and 3-nitro-benzaldehyde (3.44 g, 23 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 (3-nitro-benzylidene)-(4-trifluoromethyl-phenyl)-amine (5.88 g, 95%) as a light yellow oil: LC/MS m/e calcd for C14H9F3N2O2 (M+H)+: 295.24, observed: 295.1.

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-651309468f2d4195b603b3803b777eb7
Source dataset
uspto-grants-2013_11
Patent number
US08586747B2

Reaction notes

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