Toluene → 5,6,7,8-Tetrahydro-2-anilinoacridone

Participants

Reaction Steps

A mixture of 73.6 g (0.4 mol) of N-phenyl-p-phenylenediamine, 72 g (0.4 mol) of a mixture of the methyl and ethyl esters of 2-cyclohexanonecarboxylate (Aldrich Chemical Co., 40% methyl, 60% ethyl ester) 0.8 ml of trifluoroacetic acid and 1200 ml of toluene was refluxed for 1 hour in a flask equipped with a Dean-Stark water separator. The solvent was removed under vacuum and the resultant oil was dissolved in 500 ml of Dowtherm® A. This solution was added over 1 hour to 100 ml of refluxing Dowtherm® A in a flask equipped with mechanical stirrer, nitrogen flow and a steam heated condenser. Reflux was continued for 1 hour after the addition was complete. The mixture was cooled to room temperature and the precipitated product was filtered. The product was washed with four 200 ml aliquots of methanol. Vacuum oven drying at 80° C. overnight gave 99.9 g (89% yield) of 1,2,3,4-tetrahydro-7-(phenyl)amino-9(10H)acridinone. The product was identified by microanalysis.

Provenance & Evidence