Sodium Hydroxide → 3-Cyclopropylpyridin-2-amine

Participants

Reaction Conditions

Reaction Steps

360 mg of the methyl 3-cyclopropylpyridine-2-carboxylate [121-4] was dissolved in 4 mL of methanol, then 4 mL of 1N aqueous solution of sodium hydroxide was added thereto, and stirred at 50° C. for 30 minutes. The reaction solution was concentrated under reduced pressure, and the thus obtained residue was subjected to azeotrope twice with toluene to obtain a white solid. The obtained solid was dissolved in a mixture solvent of 4 mL of N,N-dimethylformamide and 3 mL of 1,4-dioxane, then 736 μL of triethylamine and 569 μL of diphenylphosphoryl azide were added under an ice-cold condition, and stirred at room temperature for 1 hour. Thereafter, 1.5 mL of t-butanol was added to the reaction mixture, and was stirred overnight at 80° C. After cooling the reaction mixture back to room temperature, a saturated aqueous solution of sodium hydrogen carbonate was added thereto, and extracted with chloroform. The organic layer was washed with saturated brine, and dried over anhydrous sodium sulfate. The insolubles were filtered, the filtrate was concentrated under reduced pressure, and the thus obtained residue was purified by silica gel column chromatography, to obtain 41.2 mg of 3-cyclopropylpyridine-2-amine [121-5] as a light brown oily product.

Provenance & Evidence