3-Pyridin-2-yl-propionic acid H2SO4

Synthesis

The general procedure for the synthesis of 3-pyridin-2-yl-propanoic acid from 3-(pyridin-2-yl)propan-1-ol was as follows: 3-(2-pyridinyl)-propanol (1 g, 7.6 mmol), water (13 mL), and concentrated sulfuric acid (0.59 mL, 5.1 mmol) were added to a 50 mL round-bottom flask equipped with a stirrer. Potassium permanganate (1.8 g, 11.3 mmol) was added to the stirring reaction mixture in batches over a period of 30 min while the reaction temperature was controlled at 50 °C. After the addition was completed, the reaction continued to be stirred at 50 °C until the color of the mixture changed to brown. Subsequently, the reaction mixture was warmed up to 80 °C and heated for 1 h. After completion of the reaction, it was filtered. The filtrate was concentrated to dryness under reduced pressure to afford the crude product 3-(2-pyridyl)-propionic acid (1.14 g), which could be used directly in the next step of the reaction without further purification. To obtain the pure product, the above crude product was dissolved in ethanol (10 mL), activated charcoal (0.1 g) was added, refluxed for 5 min and then hot filtered. The filtrate was cooled and crystallized to give pure 3-(2-pyridyl)-propionic acid (0.88 g, 78% yield).

References

[1] ACS Catalysis, 2018, vol. 8, # 7, p. 6738 - 6744
[2] Patent: US6162927, 2000, A
[3] Journal of Medicinal Chemistry, 2013, vol. 56, # 22, p. 9156 - 9169
[4] Journal of the American Chemical Society, 1951, vol. 73, p. 3156,3167
[5] Organic Process Research and Development, 2017, vol. 21, # 9, p. 1388 - 1393