2-{4'-[(Phenyl)amino]phenyl}aminocyclohexenecarboxylate → 9(10H)-Acridinone, 2-(phenylamino)-

Participants

Reaction Steps

Dowtherm® A (100 ml) was brought to reflux in a mechanically stirred flask with a steam-heated condenser and nitrogen atmosphere. A solution of 30 g of a mixture of the methyl and ethyl esters of 2-{4'-[(phenyl)amino]phenyl}aminocyclohexenecarboxylate in 300 ml of Dowtherm® A was added dropwise over 2 hours. Reflux was continued for 1/2 hour after the addition was complete. The reaction was cooled slightly and 1.5 g of 10% palladium on carbon was added. The mixture was refluxed for an additional 6 hours. The mixture was cooled. The precipitate that formed was filtered. The precipitate was washed with petroleum ether. The precipitate was dissolved in 150 ml of warm dimethylformamide (DMF). The DMF solution was filtered and the solid remaining on the funnel was washed with an additional 75 ml of DMF. The combined DMF filtrates were diluted to 2 liters with water. The product precipitated and was collected on a funnel and was washed well with water. Vacuum oven drying at 80° C. for 2 days gave 25 g (96% yield) of 2-(phenyl)amino-9(10H)acridinone.

Provenance & Evidence