5-Cyanopicolinic acid

Cyano-pyridine-2-carboxylic acid A 2 L stirred autoclave was charged under argon with PdC12(dppp) (2.13 g, 3.61 mmol), 6- chloro-nicotinonitrile (100 g, 0.722 mol), tert-butanol (800 ml), deionized water (200 ml) andtriethylamine (250 ml, 1.8 mol). The reaction vessel was closed, purged three times with carbonmonoxide (10 bar) and finally charged with carbon monoxide to 15 bar. The mixture was stirredvigorously at 60°C under constant pressure for 10 h; after this time no more carbon monoxideabsorption was observed. The reaction mixture was concentrated on a rotary evaporator such thatthe volatile organic components were removed. The resulting aqueous phase was filtered, extracted with dichloromethane and treated with active charcoal. After filtration, the pH of thesolution was reduced under stuffing at 60°C to ca. 0.7 by dropwise addition of hydrochloric acid.The resulting suspension was stirred at room temperature over night and then filtered. The filter cake was rinsed with water and dried in vacuo to constant weight to afford 5-cyano-pyridine-2- carboxylic acid (98.95 g) as a white solid, MS: mlz = 104 [M-C021, m.p.: 207 °C (dcc).

5-Cyanopicolinic Acid is a substituted picolinic acid tested for inhibition of DBM (Dopamine β-monooxygenase) from bovine adrenal medulla.

Molecular Weight:148.12
XLogP3:0.4
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:1
Exact Mass:148.027277375
Monoisotopic Mass:148.027277375
Topological Polar Surface Area:74
Heavy Atom Count:11
Complexity:206
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes