2,4,6-Trimethylpyridine → HCID 24902916, compound

Participants

Reaction Steps

To a solution of 2-(4-trifluoromethylbenzoyl)propanedinitrile (1.70 g, 7.15 mmol) in CH2Cl2 (60 ml), was added collidine (1.89 ml, 14.3 mmol) followed by trifluoromethanesulphonic anhydride (1.45 ml, 8.58 mmol) and the mixture stirred at room temperature for 2 h. The reaction was concentrated under reduced pressure and the residue dissolved in THF (100 ml). This was added to a suspension of tert-butyl hydrazine hydrochloride (0.98 g, 7.86 mmol) and sodium carbonate (1.14 g, 10.73 mmol) in THF and heated at reflux for 2.5h. The reaction was again concentrated under reduced pressure, the residue dissolved in ethyl acetate (100ml), washed with 2M hydrochloric acid (1×100 ml), water (1×100 ml) and brine (1×100 ml), dried (MgSO4) and solvent then removed under reduced pressure. The resulting solid was subjected to column chromatography to give the title compound (700 mg) as a pale pink solid after recrystallisation from ether, m.p. 155-156°. δH (CDCl3) 1.68 (9H, s), 4.46 (2H, br s), 7.66 (2H, d, J 8.0 Hz), and 8.03 (2H, d, J 8.0 Hz).

Provenance & Evidence