2-ACETYL-4-CYANOPHENOL

Further, the phenyl acetate was subjected to Fries Migration conditions, i.e, by heating at 180-185° C. with aluminum chloride for 3 hours, and the desired product Vc was isolated in 45percent yield.3. 2-hydroxy-5-cyanoacetophenone was obtained by acylation of 3- cyanophenol and carrying out Fries Migration. Acylation was achieved by treating the cyanophenol with acetic anhydride in the presence of catalytic amount of concentrated sulphuric acid leading to 59percent of the pure acetylated product. Further, the phenyl acetate was subjected to Fries Migration conditions, i.e, by heating at 180-185 EXAMPLE 36 Synthesis of 6-cyano-3'-[2-(2-quinolinyl)ethenyl]-flavone In a similar manner as in Example 35, the title copound represented by the following formula was obtained from 3-[2-(2-quinolinyl)ethenyl]benzaldehyde and General procedure: To a suspension of ketone (5.0 mmol, 1.0 equiv) in THF (10 mL) was added the ester (10.0 mmol, 2.0 equiv). After the reaction mixture was stirred at 0 C for about 10 min, NaH (15.0 mmol, 3.0 equiv, 60%) was added at the same temperature. Then the mixture was heated to reflux until TLC indicated the total consumption of the ketone. Removed the solvent in vacuum and the residue was mixed with ice-water (100 mL), acidified with aqueous HCl (3 M) to pH 2-3 and extracted with EtOAc (100 mL x 3). The combined organic layer was dried over sodium sulfate and evaporated under reduced pressure. The crude product was purified by flash column chromatography (EtOAc/PE = 5/95).General procedure: To a cooled (0C)solution of 2'-hydroxyacetophenone (1 g, 1 eq) in DMF (30 mL) was added phosphorusoxychloride (5 eq). The mixture stirred at 64 C for 4 h until the 2'-hydroxyacetophenone consumed completely (TLC). The reaction was quenched withglacial water (100 mL), and the mixture stirred for an additional 30 mins. Then themixture was extracted three times with dichloromethane (100 mL). And then the solventwas evaporated in vacuo and the crude product was purified by column chromatographyon silica gel.

Molecular Weight:161.16
XLogP3:1.7
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:1
Exact Mass:161.047678466
Monoisotopic Mass:161.047678466
Topological Polar Surface Area:61.1
Heavy Atom Count:12
Complexity:228
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes