Synthesis
To a three-necked flask was added 2-chloro-3-methoxypyridine (5.58 g, 39.0 mmol), N,N-dimethylformamide (60 mL) and sodium methanol (6.20 g, 115.0 mmol). The reaction mixture was stirred at 60 °C overnight. After completion of the reaction, the mixture was cooled to room temperature, water (120 mL) was added and extracted with ethyl acetate (80 mL x 3). The organic phases were combined and washed sequentially with water (100 mL x 2) and saturated brine (100 mL), then dried with anhydrous sodium sulfate. After filtration, the filtrate was concentrated by rotary evaporator to give 2,3-dimethoxypyridine (4.0 g, 28.9 mmol, 74% yield) as a yellow liquid.
References
[1] Journal of Organic Chemistry, 1994, vol. 59, # 21, p. 6173 - 6178
[2] Patent: CN107286084, 2017, A. Location in patent: Paragraph 0008
[3] Bioorganic and Medicinal Chemistry, 2003, vol. 11, # 23, p. 5083 - 5090
[4] Patent: WO2007/123995, 2007, A2. Location in patent: Page/Page column 40-41
[5] Patent: US2008/261919, 2008, A1. Location in patent: Page/Page column 18-19
