Potassium Hydroxide → 2-Pyridineacetic acid

Temperature

50 °C

To an EtOH solution (40 mL) of ethyl 2-pyridylacetate (5.00 g, 30.27 mmol, 1 equiv) was added an aqueous solution (13 mL) of KOH (2.04 g, 36.32 mmol, 1.2 equiv). The resulting solution was stirred at 50° C. (2 h). The solution was concentrated to one third of the original volume and then washed with Et2O (3×20 mL). The aqueous layer was neutralized with aqueous concentrated HCl (3.0 mL), and then concentrated in vacuo. The crude 2-(pyridin-2-yl)acetic acid (4.15 g) was used without further purification for the next step: Rf=0.06 (EtOAc); 1H NMR (DMSO-d6) δ 3.93 (s, CH2), 7.54 (dd, J=1.8, 5.4 Hz, H4), 7.60 (d, J=7.9 Hz, H6), 8.06 (dt, J=1.8, 7.9 Hz, H5), 8.64 (d, J=5.4 Hz, H3).

1. concentrationThe solution was concentrated to one third of the original volume
2. washwashed with Et2O (3×20 mL)
3. concentrationconcentrated in vacuo
4. customThe crude 2-(pyridin-2-yl)acetic acid (4.15 g) was used without further purification for the next step

ORD record

ord-88bbf80daf2143889c1136b5832dc687

Source dataset

uspto-grants-2014_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08829033B2