3-(DIMETHYLAMINO)-2-(4-METHOXYPHENYL)ACRYLONITRILE synthesis

Yield:36758-77-7 96%

Reaction Conditions:

in N,N-dimethyl-formamide; for 4 h;Reflux;

Steps:

25 Z-3-Dimethylamino-2-(4-methoxyphenyl)acrylonitrile (11a)

General procedure: To a round bottom flask, equipped with a reflux condenser and a magnetic stirring bar, was added 4-methoxybenzyl acetonitrile (0.5?g, 3.40?mmol), N,N-dimethylformamide dimethyl acetal (1.630?g, 13.6?mmol), and DMF (15?mL). The reaction mixture was refluxed for 4?h and diluted with aqueous lithium chloride (30?mL). The mixture was extracted with ethyl acetate (3?*?20?mL) and washed with aqueous lithium chloride (30?mL). The solution was dried over anhydrous sodium sulfate and the solvent was removed in vacuo to give an orange solid (0.660?g, 96% yield), which exhibited the following properties: mp 60-62?°C; ¹H NMR (CDCl₃, 300?MHz) δ 7.24 (d, J?=?8.8?Hz, 2H), 6.87 (d, J?=?8.8?Hz, 2H), 6.78 (s, 1H), 3.81 (s, 3H), and 3.22 (s, 6H); ¹³C NMR (CDCl₃, 75?MHz) δ 157.7, 149.1, 129.2, 125.5, 121.3, 114.2, 55.4 and 42.4; IR (neat) 2178 and 1620?cm^-1; HRMS (ES, M+Na) m/z calcd for C₁₂H₁₄N₂ONa 225.0998 found 225.0938.

References:

Gupton, John T.;Crawford, Evan;Mahoney, Matt;Clark, Evan;Curry, Will;Lane, Annie;Shimozono, Alex;Moore-Stoll, Veronica;Elofson, Kristen;Juekun, Wen;Newton, Micah;Yeudall, Scott;Jaekle, Elizabeth;Kanters, Rene;Sikorski, James A. [Tetrahedron,2018,vol. 74,# 52,p. 7408 - 7420]