5-CYANO-3-PYRIDINECARBOXYLIC ACID METHYL ESTER

CuCN (5.22 g, 58.3 mmol) was added to a solution of methyl 5-bromonicotinate (6 g, 27.8 mmol) in dry DMF (150 mL). Preparation 66 ;5-Cyano-nicotinic acid methyl ester; Reflux a solution of methyl 5-bromonicotinate (2.16 g, 10.0 mmol, 1 equiv) and copper (I) cyanide (1.79 g, 20.0 mmol, 2.0 equiv) in anhydr DMF (10 mL) for 15 h. After allowing to cool, filter the reaction mixture through Celite rinse with EtOAc (100 mL). A black precipitate forms in the filtrate. Wash the filtrate with salted H20 (3 x 100 mL). Dry the organic layer (anhydr Na2S04) and rotary evaporate (40 °C) giving 546 mg (33.7percent) of product as a light-yellow solid. Transfer this material to a column of silica gel (80 mm x 20 mm dia. ) and elute (20-35percent EtOAc/hex) to yield 501 mg (30.9percent) of 5- cyano-nicotinic acid methyl ester as an off-white solid. MS (m/e): 163.07 (M+1).

Molecular Weight:162.15
XLogP3:0.4
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:2
Exact Mass:162.042927438
Monoisotopic Mass:162.042927438
Topological Polar Surface Area:63
Heavy Atom Count:12
Complexity:218
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes