Isonicotinanilide

White to light yellow or grey solid

A solution of isonicotinic acid (14, 5.0 g, 40.6 mmol) in thionyl chloride (40 mL) was heated at reflux for 2 h. After completion of the reaction, thionyl chloride was removed under reduced pressure. THF (50 mL), K2CO3 (16.8 g, 121.9 mmol) and aniline (3.78 g, 40.6 mmol) were added to the residue and the reaction mixture was stirred at room temperature for 24 h. The reaction mixture was diluted with water (100 mL) and extracted with EtOAc (2 x 100 mL). The combined organic layer was concentrated and the residue was recrystallized from EtOAc-hexanes (60:40) to afford the product 15 (8.0 g, 99percent) as a light yellow solid: mp 166-168 °C. IR (KBr) 1344, 1653, 1465, 665 cm A solution of 1, 10-carbonyldiimidazole (130 g, 0.81 mol), isonicotinic acid (100 g, 0.81 mol) and DMF (300 mL) was heated at 40 C for 2.5 h before aniline (100 g, 0.81 mol) was added in a single portion. After 20 h, water (1.2 L) was added. The resulting suspension was filtered andthe solids dried under vacuum to afford isonicotinanilide (39) (142.6 g, 89percent).General procedure: A 10 mL round-bottomed flask was charged with the appropriate nitrile 2 (0.50 mmol), arylboronic acid 1(0.60 mmol), CuBr

Molecular Weight:198.22
XLogP3:1.6
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:2
Exact Mass:198.079312947
Monoisotopic Mass:198.079312947
Topological Polar Surface Area:42
Heavy Atom Count:15
Complexity:206
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes