1-oxido-4-propan-2-ylpyridin-1-ium

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a stirring solution of 139 mg (1.01 mmol) of 4-isopropylpyridine N-oxide in 10 mL of CH2Cl2 at r.t. was added 160 μL (1.20 mmol) of TMSCN. After 5 min., 100 μL (1.09 mmol) of dimethylcarbamyl chloride was added, and the solution was stirred at r.t. for 16 h. The solution was diluted with chloroform and washed with 20 mL of 10% aqueous K2CO3. The layers were separated, and the aqueous layer was extracted 3 times with CHCl3. The combined extracts were dried over Na2SO4, filtered, and concentrated. Purification by flash silica gel chromatography (30% EtOAc/hexanes) provided 4-isopropylpicolinonitrile with some impurity as a liquid. washed with 20 mL of 10% aqueous K2CO3 The layers were separated the aqueous layer was extracted 3 times with CHCl3 The combined extracts were dried over Na2SO4 filtered concentrated Purification by flash silica gel chromatography (30% EtOAc/hexanes)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of 4-isopropylpyridine and 1.5 mL of 30% H2O2 in 7 mL of AcOH was heated at 135° C. A total of 15.4 mL of H2O2 was added in 4 portions, and the solution was refluxed for 2 h. Chloroform and water were added, the layers were separated, and the aqueous layer was extracted 3 times with CHCl3. The combined extracts were dried over Na2SO4, filtered, and concentrated. Purification by flash silica gel chromatography (5% MeOH/CHCl3) provided 139 mg of the 4-isopropylpyridine N-oxide as an orange oil. the solution was refluxed for 2 h the layers were separated the aqueous layer was extracted 3 times with CHCl3 The combined extracts were dried over Na2SO4 filtered concentrated Purification by flash silica gel chromatography (5% MeOH/CHCl3)