2-Chloro-5-hydroxy-3-methylpyridine Chemical Properties

Boiling point:

353.0±37.0 °C(Predicted)

Density 

1.313±0.06 g/cm3(Predicted)

storage temp. 

Inert atmosphere,Room Temperature

pka

8.81±0.10(Predicted)

Appearance

White to light yellow Solid

CAS DataBase Reference

54232-03-0

Safety Information

HS Code 

2933399990

2-Chloro-5-hydroxy-3-methylpyridine Usage And Synthesis

Synthesis

To a stirred solution of methanol (15 mL) was added potassium carbonate (1.10 g, 0.0081 mol) as 6-chloro-5-methylpyridin-3-yl acetate (750 mg, 0.004 mol) at room temperature. The reaction mixture was stirred continuously at ambient temperature for 1 hour. Subsequently, the solvent was removed by concentration under reduced pressure and the residue was diluted with a minimal amount of water and neutralized with 1N hydrochloric acid (15 mL). After neutralization was complete, the solution was extracted using ethyl acetate (2 x 100 mL). The combined organic layers were washed with brine, dried over anhydrous sodium sulfate and concentrated to give 6-chloro-5-methylpyridin-3-ol as an off-white solid (500 mg, 89% yield). Mass spectrometry analysis showed m/z = 143.01 [M + H]+. 1H-NMR (300 MHz, DMSO-d6) data were as follows: δ 10.09 (s, 1H), 7.76 (d, J = 3Hz, 1H), 7.18 (d, J = 3.6Hz, 1H), 2.24 (s, 3H).

References

[1] Patent: WO2014/138484, 2014, A1. Location in patent: Page/Page column 157
[2] Patent: WO2016/22724, 2016, A1. Location in patent: Page/Page column 297
[3] Patent: US2014/249104, 2014, A1. Location in patent: Page/Page column

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