P-Anisidine → 2-[1-(2,4,6-Trimethylphenylimino)ethyl]-6-[1-(4-methoxyphenylimino)ethyl]pyridine

HRID 49752Notes

Reaction equation

HRID 49752 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].[CH3:22][O:23][C:24]1[CH:30]=[CH:29][C:27]([NH2:28])=[CH:26][CH:25]=1>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:28][C:27]2[CH:29]=[CH:30][C:24]([O:23][CH3:22])=[CH:25][CH:26]=2)[CH3:20])[N:14]=1)[CH3:12]

Participants

4

Reactant 2

HCID 7732P-AnisidineHCID 221344681-{6-[(1E)-N-(2,4,6-Trimethylphenyl)ethanimidoyl]pyridin-2-yl}ethan-1-one

Product 1

HCID 213000512-[1-(2,4,6-Trimethylphenylimino)ethyl]-6-[1-(4-methoxyphenylimino)ethyl]pyridine

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Monoimine (1, 280 mg, 1 mmol) and 4-methoxyaniline (123 mg, 1 mmol) were dissolved in 20 ml of toluene. To this solution 4 Å molecular sieves were added. After standing for 6 days at room temperature the reaction mixture was filtered and the solvent was removed in vacuo. The residue was recrystallised from ethanol. Yield 148 mg (38%) of mixed diimine (6). 1H-NMR (CDCl3) δ 8.42 (dd, 1H), 8.34 (dd, 1H), 7.86 (t, 1H), 6.93 (d, 2H), 6.88 (s, 2H), 6.81 (d, 2H), 3.82 (s, 3H), 2.43 (s, 3H), 2.29 (s, 3H), 2.22 (s, 3H), 2.00 (s, 6H).

Workup

  1. additionTo this solution 4 Å molecular sieves were added
  2. filtrationthe reaction mixture was filtered
  3. customthe solvent was removed in vacuo
  4. customThe residue was recrystallised from ethanol

Sources & evidence

ORD record
ord-cdd99e7493c24c1b835a9f1bd372e427
Source dataset
uspto-grants-2004_03
Patent number
US06710006B2

Reaction notes

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