Dimethyl Sulfate → 2,6-Dimethylpyridine-4-carbonitrile

Participants

Reaction Conditions

Reaction Steps

To a stirred quantity of 2,6-lutidine-1-oxide (12.3 g, 100 mmol) was slowly added dimethyl sulphate (12.6 g, 100 mmol) at such a rate that the temperature of the reaction mixture was maintained at 80° C. throughout the addition. When the addition was complete (about one hour) the solution was stirred at that temperature for an additional 2 h. The salt crystallised upon cooling and was recrystallised from anhydrous acetone giving white prisms; m.p 96-97° C. Yield 18 g (73%). To a solution of this 1-methoxy-2,6-dimethylpyridinium methyl sulphate (11.65 g, 50 mmol) dissolved in water (50 ml), under nitrogen, was added a solution of potassium cyanide (10 g, 150 mmol) dissolved in 50 ml of water. The solution was allowed to stand at room temperature for 2 days at which time the nitrile, which had separated from the solution as long white needles, was removed by filtration, yielding 2.8 g of pure product (42%) δH (CDCl3, 500 MHz) 2.44 (6 H, s, 2×CH3), 4.2 (2 H, d, J 5, NHCH2), 6.78 (2 H, s, ArH); δC (CDCl3, 500 MHz) 157.83 (2×C), 122.71 (C), 118.2 (2×CH), 24.28 (2×CH3)

Provenance & Evidence