Phenol → 5,6-Dihydroimidazo[4,5,1-jk][1]benzazepine-2,7(1H,4H)-dione

Participants

Reaction Conditions

Reaction Steps

A mixture of 29.2 g of the product of Step C, 292 g of o-phosphoric acid and 14.1 g of phenol were heated at 150° C. under an inert atmosphere for 2 hours, was cooled to about 35° C. and was poured into 1200 ml of iced water with stirring. 2 liters of methylene chloride were added to the mixture which was then made alkaline with sodium hydroxide. The mixture was filtered and the solids were washed with methylene chloride. The combined organic phases were washed, dried and evaporated to dryness under reduced pressure. The residue was crystallized and was chromatographed over silica gel. Elution with a 90-2-2 ethyl acetate-methanol-triethylamine mixture yielded 9.7 g of 5,6-dihydro-imidazo[4,5,l-j-k][1]benzazepin-2,7-[1H,4H]-dione melting at 235° C.

Provenance & Evidence