Ammonia → 6-Methyl-3-phenylquinolin-2(1H)-one

Participants

Reaction Conditions

Reaction Steps

0.41 ml (5.3 mmol, 1.5 eq) of N,N-dimethylformamide is added dropwise to 3.3 ml (25 mmol, 7 eq) of POCl3, under a nitrogen atmosphere and at −30° C. The medium is stirred for 15 min at −30° C. and 800 mg of amide 47 (3.5 mmol) are then added. The reaction mixture is warmed to room temperature with stirring and the reaction is then heated at 75° C. for 1.5 h. At the end of the reaction, this solution is poured onto crushed ice, neutralized with aqueous 30% ammonia solution and then extracted with dichloromethane. The organic phase is dried over MgSO4 and then evaporated. The residue obtained is dissolved in 5.4 ml of glacial acetic acid and 0.2 ml of water and the final solution is then refluxed for 3 h. The acetic acid is evaporated off. The residue is dissolved in water, neutralized with 25% sodium hydroxide solution and then finally extracted with dichloromethane. The organic phase is dried over MgSO4 and then evaporated under reduced pressure. The residue is taken up in ethyl acetate, which brings about precipitation of the final product. The crystals thus obtained are filtered off to give 80 mg (10%) of compound 48.

Provenance & Evidence