1H-1-ACETYLIMINO-3-METHYLBENZO[C]PYRAN-4-CARBONITRILE synthesis

Yield:161468-31-1 91%

Reaction Conditions:

with sodium acetate for 2 h;Reflux;

Steps:

N-(4-Cyano-3-methyl-1H-isochromen-1-ylidene)acetamide

Prepared according to the original method of Gabriel andNeumann44 with reference to the corrected structure.38 A mixtureof 2-cyanophenylacetonitrile 14 (5.0 g, 35 mmol) and anhydroussodium acetate (2.5 g) in distiled acetic anhydride (25 mL) wasrefluxed for 2 h. The resulting mixture was poured onto ice andstirred for 0.25 h. The precipitate was filtered, washed with H2Oand dried to give amide 15 as a brown solid (7.2 g, 91%), mp135-136 C (from CCl4) (lit.44 137-138 C). dH (CDCl3): 8.13 (1H,d, J 8.0 Hz), 7.74-7.70 (1H, m), 7.58 (1H, d, J 8.0 Hz), 7.53-7.49(1H, m), 2.50 (3H, s), 2.31 (3H, s). dC (CDCl3): 182.7, 163.7, 145.9,134.6, 130.0, 129.7, 128.2, 123.5, 119.8, 114.3, 92.7, 25.9, 19.5.

References:

Buskes, Melissa J.;Harvey, Katherine L.;Prinz, Boris;Crabb, Brendan S.;Gilson, Paul R.;Wilson, David J.D.;Abbott, Belinda M. [Bioorganic and Medicinal Chemistry,2016,vol. 24,# 11,p. 2389 - 2396]