Acetone → Methyl 5-cyanopyridine-3-carboxylate

Participants

Reaction Conditions

Reaction Steps

3-Cyano-5-ethynylpyridine (1.28 g) (see Example 2) was dissolved in acetone (20 ml), and an aqueous solution (40 ml) of potassium permanganate (350 mg) was added dropwise. After the addition was completed, the reaction mixture was heated to 100° C. and filtered. The filtrate was concentrated under reduced pressure, and the residue was dissolved in DMF (20 ml). Potassium carbonate (1.6 g) and dimethyl sulfate (1 ml) were added to the solution, and the mixture was stirred at room temperature for 10 minutes. Water (10 ml) was added to the reaction mixture, and resulting mixture was extracted with diethyl ether (30 ml×3). The diethyl ether layer was dried over anhydrous sodium sulfate, concentrated under reduced pressure and purified by silica gel column chromatography (Wako Gel C-200, 10 g; eluted with hexane:diethyl ether=1:1) to give 5-carbomethoxy-3-cyanopyridine (670 mg; yield, 41%) as colorless solids. IR (KBr) cm-1 : 2210, 1730.

Provenance & Evidence