3-Pyridinecarbonitrile,5-hydroxy-(9CI) Chemical Properties

Melting point:

213-217℃

Boiling point:

394.7±27.0 °C(Predicted)

Density 

1.33±0.1 g/cm3(Predicted)

storage temp. 

Inert atmosphere,Room Temperature

pka

7.96±0.10(Predicted)

Appearance

Off-white to light yellow Solid

Water Solubility 

Slightly soluble in water.

InChI

InChI=1S/C6H4N2O/c7-2-5-1-6(9)4-8-3-5/h1,3-4,9H

InChIKey

KAXIYYPIORYZLB-UHFFFAOYSA-N

SMILES

C1=NC=C(O)C=C1C#N

CAS DataBase Reference

152803-24-2

Safety Information

RIDADR 

3439

HazardClass 

6.1

PackingGroup 

Ⅲ

HS Code 

2933399990

3-Pyridinecarbonitrile,5-hydroxy-(9CI) Usage And Synthesis

Uses

3-Cyano-5-hydroxypyridine is active pharmaceutical ingredients.

Synthesis

General procedure for the synthesis of 3-cyano-5-hydroxypyridine from 5-methoxynicotinonitrile: 1 g of 5-methoxynicotinonitrile (7.46 mmol) was mixed with 8.62 g of pyridine hydrochloride, and the reaction was heated at 200 °C for 2 hours. After completion of the reaction, the crude product was diluted with water and extracted several times with ether. The aqueous phase was alkalized by addition of sodium bicarbonate and extracted again with ether. The organic phases were combined, dried over anhydrous sodium sulfate and concentrated under reduced pressure to give 850 mg of 5-hydroxynicotinonitrile as a beige solid in 95% yield. The product was analyzed by LC-MS: m/z 120.94 (M+H+). 1H NMR (400 MHz, DMSO-d6): δ 10.79 (s, 1H, OH), 8.46 (s, 1H, Harom.), 8.42 (s, 1H, Harom.), 7.60 (s, 1H, Harom.).

References

[1] Patent: WO2012/101239, 2012, A1. Location in patent: Page/Page column 74
[2] Patent: US2013/85144, 2013, A1. Location in patent: Paragraph 0394; 0395; 0396
[3] Patent: EP2689778, 2014, A1. Location in patent: Paragraph 0238
[4] Patent: WO2014/16433, 2014, A1. Location in patent: Page/Page column 73
[5] Patent: WO2014/16434, 2014, A1. Location in patent: Page/Page column 72

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