4-CYANO-2-METHOXYPYRIDINE

2-(Methyloxy)-4-pyridinecarbonitrile; To a solution of 2-chloro-4-cyanopyridine (1.38 g, 10 mmol) in dioxane (10 mL) was added a solution of sodium methoxide in methanol (25percentw, 2.27 g, 10.5 mmol). The reaction mixture was heated at reflux for 5 hours, then cooled to room temperature and left over night in refrigerator. The precipitate was filtered and washed with methanol. The filtrate was concentrated down to about 10 mL, and water (100 mL) was added. The precipitates was collected by filtration and washed with water to afford the title compound (1.93 g, 72percent) as a white solid. MS (ES+) m/z 135 [M+H]Synthesis of 2-methoxy-isonicotinonitrile; A stirred suspension of 17.86 g NaOMe (330.7 mmol, 1.22 eq) in 95 mL acetonitrile was cooled to 0° C and a solution of 37.56 g 2-chloro-4-cyano pyridine (8, 271.1 mmol) in 225 mL acetonitrile was added over 45 min. Stirring was continued at room temperature for 23 h until less than 4 percent (area) starting material were detected by HPLC. 11.1 g potassium dihydrogen phosphate (81.56 mmol, 0.30 eq) were added at 0° C and stirring was continued for 3 h at room temperature. The reaction mixture was then evaporated to dryness in a rotary evaporator (40°C/10 mbar) yielding the crude product (64.94 g, 179 percent by weight) as a brown solid. 64.94 g crude product were extracted with 900 mL toluene for 18 h at reflux temperature using a soxhlet extraction apparatus yielding the title product (25.65 g, 71 percent by weight) as an orange solid. Mr(a) (i)

Molecular Weight:134.14
XLogP3:1.1
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:1
Exact Mass:134.048012819
Monoisotopic Mass:134.048012819
Topological Polar Surface Area:45.9
Heavy Atom Count:10
Complexity:149
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes