methyl pyridine-3-acetate Chemical Properties

Boiling point:

112 °C(Press: 10 Torr)

Density 

1.115±0.06 g/cm3(Predicted)

storage temp. 

Inert atmosphere,Room Temperature

pka

4.40±0.11(Predicted)

Appearance

Light yellow to yellow Liquid

methyl pyridine-3-acetate Usage And Synthesis

Synthesis

To synthesize methyl (pyridin-3-yl)acetate, the following procedure was used: in a 1L four-necked flask equipped with a nitrogen introduction tube, thermometer, Dimroth condenser, and a dropping funnel, 25.12 g (0.145 mol) of pyridine-3-acetic acid hydrochloride was added. Subsequently 500mL of anhydrous methanol was added. Stir at room temperature under nitrogen protection until the hydrochloride is completely dissolved. 31.12 g (0.248 mol) of thionyl chloride was slowly added dropwise. After the dropwise addition was completed, the reaction mixture was heated to reflux and the reaction was continued for 2.5 hours. After completion of the reaction, the mixture was cooled to room temperature and methanol was removed by distillation under reduced pressure by rotary evaporator. The residue was neutralized to pH neutral with saturated aqueous sodium bicarbonate. The aqueous phase was extracted with 100 mL of ethyl acetate in three fractions, the organic phases were combined and dried over anhydrous sodium sulfate. After filtration to remove the desiccant, the solvent was removed by distillation under reduced pressure to give 21.29 g (0.141 mol) of methyl (pyridin-3-yl)acetate in 97% yield.

References

[1] Patent: EP2390243, 2011, A1. Location in patent: Page/Page column 26
[2] Tetrahedron Letters, 1993, vol. 34, # 2, p. 331 - 334

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