6-Chloro-3-Methylpyridine-2-carboxylic Acid Chemical Properties

Boiling point:

333.7±37.0 °C(Predicted)

Density 

1.390±0.06 g/cm3(Predicted)

storage temp. 

under inert gas (nitrogen or Argon) at 2-8°C

pka

2.93±0.32(Predicted)

Appearance

White to off-white Solid

Safety Information

WGK Germany 

3

HS Code 

2933399990

6-Chloro-3-Methylpyridine-2-carboxylic Acid Usage And Synthesis

Uses

6-Chloro-3-methylpyridine-2-carboxylic Acid is disubstituted pyridinecarboxylic acid used in the preparation of biologically active compounds such as inhibitors of Janus kinases and PDK1.

Synthesis

An aqueous 2N NaOH solution (5 mL) was slowly added dropwise to a stirred solution of methyl 6-chloro-3-methylpyridine-2-carboxylate (0.500 g, 2.702 mmol) in tetrahydrofuran (THF, 10 mL) at 0 °C. The reaction mixture was then warmed to 50 °C with continuous stirring for 2 hours. Upon completion of the reaction, the mixture was acidified to pH < 7 with aqueous citric acid and subsequently extracted with ethyl acetate (EtOAc, 2 × 10 mL). The organic phases were combined, dried with anhydrous sodium sulfate, filtered and concentrated under reduced pressure to afford 6-chloro-3-methylpyridine-2-carboxylic acid as an off-white solid (0.45 g, 97% yield). The resulting product could be used in the subsequent reaction without further purification. Mass spectrometry (MS) analysis showed the molecular ion peak (m/z) of the target compound: 172.0 ([M+H]+).

References

[1] Patent: WO2015/94912, 2015, A1. Location in patent: Page/Page column 12
[2] Patent: WO2014/4230, 2014, A1. Location in patent: Page/Page column 8; 45

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