2-Pyridineacetic acid, methyl ester

Clear yellow liquid

S2 was prepared analogously to a published procedure.13 2.00 g S1 (11.5 mmol, 1.00 equiv.) and 14 mL MeOH were added to a round-bottom flask. The solution was cooled to 0 °C, and 2.90 mL TMSCl (23.0 mmol, 2.00 equiv.) were added dropwise. The mixture was allowed to warm to room temperature and stirred overnight. The solvent was then removed in vacuo, ant the remaining solid was treated slowly with sat. aq. NaHCO3 (40 mL). The aqueous solution was extracted with CH2Cl2 (4 x 40 mL), and the combined organic extracts were dried over Na2SO4, filtered, and the solvent was removed in vacuo. The crude product (S2) was isolated as a clear oil (1.73 g, 11.47 mmol, quant.). The spectral data of the compound were compared with the published ones.13To a solution of 2-(pyridin-2-yl)acetic acid hydrochloride salt MMMMMM (50.0 g, 288.0 mmol, 1.0 equiv.) in methanol (500 mL, 0.5M) at 0 °C was added thionyl chloride (31.5 mL, 432.0 mmol, 1.5 equiv.) dropwise. The reaction was stirred at 0 °C for 60 minutes or until the reaction was determined to be complete by LCMS or TLC. The reaction was carefully quenched with sodium carbonate and the aqueous layer extracted with ethyl acetate. The combined organic layers were washed with water, brine, dried over magnesium sulfate, filtered, and concentrated in vacuo. The resulting product (NNNNNN, 41.5 g, 275.0 mmol, 95percent) was used in the next step without further purification.Step 1: To a solution of 2-(pyridin-2-yl)acetic acid hydrochloride salt MMMMMM (50.0 g, 288.0 mmol, 1.0 equiv.) in methanol (500 mL, 0.5M) at 0° C. was added thionyl chloride (31.5 mL, 432.0 mmol, 1.5 equiv.) dropwise. The reaction was stirred at 0° C. for 60 minutes or until the reaction was determined to be complete by LCMS or TLC. The reaction was carefully quenched with sodium carbonate and the aqueous layer extracted with ethyl acetate. The combined organic layers were washed with water, brine, dried over magnesium sulfate, filtered, and concentrated in vacuo. The resulting product (NNNNNN, 41.5 g, 275.0 mmol, 95percent) was used in the next step without further purification.

Molecular Weight:151.16
XLogP3:0.3
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:3
Exact Mass:151.063328530
Monoisotopic Mass:151.063328530
Topological Polar Surface Area:39.2
Heavy Atom Count:11
Complexity:136
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes