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To a solution of 3-picoline (50 g, 0.48 mol) in glacial acetic acid (150 ml) was added hydrogen peroxide (25 ML) at RT. The mixture was heated to 90C for 3 hr. The mixture was cooled to RT and more hydrogen peroxide (18.5 ml) was added slowly. The mixture was again heated to 90OC for 19 hr. The excess peroxide was carefully decomposed using Pd-C (2.5 g) at 0C. Pd-C was removed by filtration, and the filtrate was concentrated and crude 3-methyl pyridine-1-oxide was purified by fractional distillation in vacuo. [00144] A solution of 3-methyl pyridine-1-oxide (10 g, 0.092 mol) in methyl iodide (15 ml) was left at rt for 18 hr and the solid was filtered. The filtrate was diluted with diethyl ether and extracted with water (40 ML). The solid was re-dissolved in the aqueous extract, 1,4-dioxane (50 ml) was added, followed by potassium cyanide (15 g, 0.23 mol) and the mixture was stirred at RT for 3 hr. The product was extracted with chloroform. The chloroform layer was washed with water, brine and dried over sodium sulfate. The solvent was removed in vacuo and the crude product was purified by fractional distillation (61-62C/0. 2 mm) to yield a white low melting solid. [00145] BC13 (24 ml, 1 M in DCM, 0.024 mol) was added slowly to a solution of 4-chloroaniline (2 g, 0.016 mol) in 30 ml of trichloroethylene over a period of 15 min. at 0C and stirred at this temperature for an additional 10 min. 4-Cyano-3-methylpyridine (2.2 g, 0.019 mol) and AIC13 (3 g, 0.022 mol) were added at 0C. The solution was allowed to warm to RT and stirred for 30 min. The solution was then heated at 80-90C for 1 hr. and the DCM was distilled off. The resulting solution was REFLUXED at 115C for 4 hr and stirred at RT overnight. 3N HCI (20 ML) was added and the mixture REFLUXED at 100C for 2 hr. The reaction mixture was cooled to 0C and adjusted to pH-12 with 6N NaOH. The reaction mixture was extracted with DCM., and the DCM layer washed with water, brine and dried over NA2SO4. The solvent was removed, and the crude was purified by column chromatography over silica gel to yield a yellow solid.
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