4-CYANO-PYRIDINE-2-METHANOL

Sulfuric acid (1.5 ml) was added to the solution of 4-cyanopyridine (15.7 g, 151 mmol) in methanol (225 ml) at room temperature and refluxed for 30 minutes. A solution of ammonium peroxodisulfate (54.9 g, 241 mmol) in HAdd ammonium persulfate (70.1 g, 307 mmol) to a solution of isonicotinonitrile (16.00 g, 154 mmol) in methanol: water: sulfuric acid (275 mL:135 mL:l 1 mL). Heat solution to reflux. After 24 hours, pour reaction onto ice and neutralize with ammonium hydroxide (70 ml). Extract solution with chloroform (3x600 ml). Combine the organic layers, dry with sodium sulfate, filter, and concentrate under reduced pressure to give a residue. Purify the residue by flash chromatography eluting with acetone :dichloromethane (1:6) to yield the title compound as a white solid (5.86 g, 28percent): A) 1N HTo a stirred solution of 4-cyanopyridine (10.4g, 100.0mmol) in methanol (100mL) and water(50ml_) at room temperature was added cone sulfuric acid (5mL), a slight exotherm was noted. After 10 minutes iron sulphate heptahydrate (910mg, 3.0mmol) was added and the reaction immediately turned a dark yellow / orange. After sonication of the reaction mixture under nitrogen for 20 minutes, hydroxylamine -O-sulfuric acid (11.3g, lOO.Ommol) was added in one portion. A slight exotherm was noted after 10 minutes, the reaction was maintained under a nitrogen atmosphere.After 2 hours additional hydroxylamine-O-sulfuric acid (11.3g, lOO.Ommol) was added together with cone sulfuric acid (5mL) and iron(ll)sulphate heptahydrate (910mg, 3.0mmol). After a further 3 hours of stirring the reaction was neutralized by addition of sodium carbonate (18.0g 200mmol). The mixture was then diluted with water (100ml) and filtered to remove a deep red / brown ppt, the filtrate was concentrated to dryness and the resulting solid dissolved in water (50ml_) and extracted with EtOAc (5x 100ml). The combined organics were dried over MgS0

Molecular Weight:134.14
XLogP3:-0.4
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:1
Exact Mass:134.048012819
Monoisotopic Mass:134.048012819
Topological Polar Surface Area:56.9
Heavy Atom Count:10
Complexity:149
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes