Diethylcarbamoyl chloride → 5,6-Dimethylpyridine-2-carbonitrile

Participants

Reaction Steps

To a slurry of N-oxide from Step 1 (8.7 g) in CH2Cl2 (125 mL) at r.t. was added trimethylsilylcyanide (9.9 mL, 74.2 mmol). After stirring for 15 minutes, N,N-diethylcarbamoyl chloride (9.4 mL, 74.2 mmol) was added and the resulting mixture was allowed to stir at r.t. for 2.5 days. The reaction was quenched by careful addition of 10% aq. K2CO3, stirred 15 minutes, and extracted (3×) with CH2Cl2. The organic layer was washed with aq. K2CO3, brine, and dried over Na2SO4 /K2CO3. Evaporation of the solvent and purification of the residue by flash chromatography (25% to 50% Et2O in hexanes) yielded 4.13 g of the title compound.

Provenance & Evidence