5-Hydroxy-3-methylpyridine-2-carbonitrile

Sodium nitrite (1.6 M aqueous solution containing 10.3 g of sodium nitrite, 149 mmol) was slowly added to a 0 °C solution of C35 (18.0 g, 135 mmol) in water (243 mL) and concentrated sulfuric acid (67.5 mL). The reaction mixture was warmed to room temperature and then stirred at 100 °C for 3 hours, whereupon it was cooled and extracted with ethyl acetate (3 x 75 mL). The combined organic layers were washed with water (2 x 75 mL) and with saturated aqueous sodium chloride solution (2 x 75 mL), dried, filtered, and concentrated under reduced pressure to afford the product as a yellow solid. Yield: 16 g, 120 mmol, 89percent.Sodium nitrite (1.6 M aqueous solution containing 10.3 g of sodium nitrite, 149 mmol) was slowly added to a 0 °C solution of C29 (18.0 g, 135 mmol) in water (243 mL) and concentrated sulfuric acid (67.5 mL). The reaction mixture was warmed to room temperature and then stirred at 100 °C for 3 hours, whereupon it was cooled and extracted with ethyl acetate (3 x 75 mL). The combined organic layers were washed with water (2 x 75 mL) and with saturated aqueous sodium chloride solution (2 x 75 mL), dried, filtered, and concentrated under reduced pressure to afford the product as a yellow solid. Yield: 16 g, 120 mmol, 89percent.Sodium nitrite (1.6 M aqueous solution containing 10.3 g of sodium nitrite, 149 mmol) was slowly added to a 0 °C solution of 5-amino-3-methylpicolinonitrile (048)(18.0 g, 135 mmol) in water (243 mL) and concentrated sulfuric acid (67.5 mL). The reaction mixture was warmed to room temperature and then stirred at 100 °C for 3 hours, whereupon it was cooled and extracted with ethyl acetate (3 x 75 mL). The combined organic layers were washed with water (2 x 75 mL) and with saturated aqueous sodium chloride solution (2 x 75 mL), dried, filtered, and concentrated underreduced pressure to afford 5-hydroxy-3-methylpicolinonitrile as a yellow solid. Yield: 16 g, 120 mmol, 89percent. 1H NMR (400 MHz, DMSO-d6) o 11.07 (brs, 1H), 8.08 (d, J=2.6 Hz, 1H), 7.20 (d, J=2.3 Hz, 1H), 2.40 (s, 3H).A resealable vessel was charged with Pd

Molecular Weight:134.14
XLogP3:0.9
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:3
Exact Mass:134.048012819
Monoisotopic Mass:134.048012819
Topological Polar Surface Area:56.9
Heavy Atom Count:10
Complexity:160
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes