3-(4-Fluorophenyl)-3-oxo-2-(4-pyridinyl)propanenitrile synthesis

Yield:148671-42-5 103%

Reaction Conditions:

with hydrogenchloride;potassium carbonate in N-methyl-acetamide;water;

Steps:

34.a (a)

(a) Synthesis of 3-(4-fluorophenyl)-3-oxo-2-(4-pyridyl)propionitrile 32 g of 4-pyridylacetonitrile and 86 g of 2,5-dioxo-pyrrolidinyl 4-fluorobenzoate were dissolved in 1.3 L of dimethylformamide. After the addition of 164 g of potassium carbonate, the resulting mixture was stirred at room temperature for a day. After the reaction mixture was filtered through cerite, the filtrate was concentrated under reduced pressure. After water was added to the residue, this solution was neutralized with an aqueous solution of hydrochloric acid. The precipitated crystals were collected by filtration, washed with diethyl ether, and then dried in a stream of air to obtain 67 g (103% yield) of the title compound. Melting point: 220.0-223.0° C. (decomp.) ¹H-NMR (CD₃OD) δ: 8.23-7.97 (m, 4H), 7.80-7.61 (m, 2H), 7.12 (t, J=8.9 Hz, 2H) IR (KBr) ν max: 2180, 1636, 1608, 1542, 1492, 1408, 1374, 1342, 1222, 1202, 1156, 830 cm-^-1 Mass, m/e: 240 (M⁺), 123 (base)

References:

US6511997,2003,B1