2,6-Dichloroaniline → 2,6-Bis-[(2,6-dichlorophenylimino) methyl]pyridine

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Reaction Steps

2,6-Pyridinedicarboxaldehyde (1 g, 7.4 mmol) and 2,6-dichloroaniline (2.6 g, 16.0 mmol) were dissolved in 100 ml of toluene. To this solution 4 Å molecular sieves were added. After standing for 2 days, with addition of more 4 Å molecular sieves the mixture was filtered. The solvent was removed in vacuo. The residue was crystallised from ethanol. Yield 1.4 g (45%) of 6. 1H-NMR (CDCl3) δ 8.53 (s, 2H, HC═N), 8.45 (d, 2H, Py-Hm), 8.02 (t, 1H, Py-Hp), 7.36 (d, 4H, ArH), 7.03 (t, 2H, ArH).

Provenance & Evidence