2-Fluoroaniline → 2-[1-(2,4,6-Trimethylphenylimino) ethyl]-6-[1-(2-fluorophenylimino)ethyl]pyridine

HRID 349596Notes

Reaction equation

HRID 349596 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4]([CH3:9])[C:3]=1[N:10]=[C:11]([C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([C:19](=O)[CH3:20])[N:14]=1)[CH3:12].[F:22][C:23]1[CH:29]=[CH:28][CH:27]=[CH:26][C:24]=1[NH2:25]>C1(C)C=CC=CC=1>[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4]([CH3:9])[C:3]=1[N:10]=[C:11]([C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([C:19](=[N:25][C:24]2[CH:26]=[CH:27][CH:28]=[CH:29][C:23]=2[F:22])[CH3:20])[N:14]=1)[CH3:12]

Participants

4

Reactant 2

HCID 95842-FluoroanilineHCID 221344681-{6-[(1E)-N-(2,4,6-Trimethylphenyl)ethanimidoyl]pyridin-2-yl}ethan-1-one

Product 1

HCID 213000492-[1-(2,4,6-Trimethylphenylimino) ethyl]-6-[1-(2-fluorophenylimino)ethyl]pyridine

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
50 °C

Procedure

Monoimine (1, 1.0 g, 3.57 mmol) and 2-fluoroaniline (398 mg, 3.57 mmol) (ex. Aldrich) were dissolved in 50 ml of toluene. To this solution, 4 Å molecular sieves were added. After standing for 20 hrs., with addition of more molecular sieves, the mixture was filtered. The solvent was removed in vacuum and the oily residue was warmed in ethanol (50° C.). The yellow solid, which precipitated after cooling at −20° C., was filtered off and dried in vacuo. Yield 300 mg (23%) of mixed diimine (4).

Workup

  1. additionTo this solution, 4 Å molecular sieves were added
  2. addition, with addition of more molecular sieves
  3. filtrationthe mixture was filtered
  4. customThe solvent was removed in vacuum
  5. customThe yellow solid, which precipitated
  6. temperatureafter cooling at −20° C.
  7. filtrationwas filtered off
  8. customdried in vacuo

Sources & evidence

ORD record
ord-591d5f8c91894dee8d4ebe845bb3b96b
Source dataset
uspto-grants-2007_02
Patent number
US07179871B2

Reaction notes

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