16858-01-8

White to dark yellow solid

GENERAL STEPS: Under nitrogen protection, 2-chloromethylpyridine hydrochloride (2.0 g, 12.2 mmol) was placed in a 100 mL aubergine flask and dissolved in 20 mL of distilled water. The reaction vial was placed in an ice bath and a solution prepared from NaOH (2.44 g, 61.0 mmol) dissolved in a minimal amount of distilled water was added slowly and dropwise. Subsequently, 2-aminomethylpyridine (0.60 g, 5.54 mmol) was added and stirred until the solution was homogeneous (a small amount of distilled water was added if necessary). At this point the solution was red in color. The ice bath was removed and the reaction mixture was stirred at room temperature for 48 hours, during which time the color of the solution gradually changed to brown and a brown oil precipitated. 50 mL of dichloromethane was added to the reaction mixture, transferred to a split funnel and extracted with dichloromethane (50 mL x 3). The organic layers were combined, dried with anhydrous sodium sulfate and concentrated under reduced pressure to give a brown oil. The oil was dried under vacuum to give a brown semi-solid. After washing with a small amount of ether, a brown solid was obtained. Recrystallization by petroleum ether gave 0.68 g of light yellow needle-like crystals in 42% yield.

[1] Chemistry - A European Journal, 2017, vol. 23, # 51, p. 12550 - 12558
[2] RSC Advances, 2016, vol. 6, # 108, p. 106248 - 106259
[3] Patent: JP2017/197451, 2017, A. Location in patent: Paragraph 0037