3-Hydroxy-2-pyridinecarbonitrile

5.0 g of 1N hydrochloric acid and 1.0 g (6.31 mmol) of' -amino-2-furanacetonitrile hydrochloride were added to a three-necked flask at room temperature. The mixture was cooled to 0 ° C, and 360 μM of bromine (6.94 mmol) was added dropwise thereto, followed by stirring for 1 hour. The resulting mixture was warmed to room temperature and stirred for 2 hours. The obtained mixture was stirred for 2 hours, bromine 32pL was added, and the mixture was stirred for another 2 hours. Then, 32 pL of bromine was added and the mixture was stirred for 1 hour To the resulting mixture, 199 mg of sodium thiosulfate was added, followed by addition of a 40percent aqueous NaOH solution, and the pH was adjusted to 3.0. The obtained mixture was filtered to obtain a mixture containing 0.47 g of 2-cyano-3-hydroxypyridine. The yield of 2-cyano-3-hydroxypyridine was 62percent based on the hydrochloride of alpha-amino-2-furanacetonitrileUnder a nitrogen atmosphere, in a three-necked flask, 0.51 g of 2-cyano-3-hydroxypyridine, 5.0 ml of acetonitrile, 500 muL of pyridine and 0.90 g of toluenesulfonyl chloride were added. The obtained mixture was stirred at room temperature for 3 hours, then water and toluene were added, And separated. After concentrating the obtained organic layer, The obtained mixture was purified using column chromatography (hexane: ethyl acetate = 9/1 ' 6/4)0.95 g of 2-cyano-3- (4-methylbenzenesulfonyloxy) pyridine was obtained.Under a nitrogen atmosphere, a three-necked flask was charged with 5 mL of toluene, 1.04 g of 2-cyano-3-hydroxypyridine, 1.7 g of potassium carbonate and 0.8 mL of methanesulfonyl chloride were added, And the mixture was stirred for 3.5 hours. The resulting mixture was stirred at 50 C. for 2 hours, 2 mL of acetonitrile was added, And the mixture was further stirred for 2 hours. Toluene and water were added to the obtained mixture, And separated. By concentrating the obtained organic layer, 1.61 g of 2-cyano-3-methanesulfonyloxypyridine was obtained.

Molecular Weight:120.11
XLogP3:1.1
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:3
Exact Mass:120.032362755
Monoisotopic Mass:120.032362755
Topological Polar Surface Area:56.9
Heavy Atom Count:9
Complexity:137
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes