Nitric Acid → 3,4-Dihydro-9-methylamino-7-nitroacridin-1(2H)-one

Participants

Reaction Steps

In 100 ml of concentrated H2SO4 at 0° C. was added 4.83 g of 3,4-dihydro-9-(methylamino)acridin-1(2H)-one. While maintaining the reaction at 0° C., 1.92 ml (1 eq) of concentrated HNO3 (70 wt %) was added dropwise over 10 minutes. Since the reaction appeared complete after the addition based on thin layer chromatography, the reaction mixture was poured into ice and neutralized with 50% NaOH. At the basic point a precipitate formed. This was filtered and chromatographed on silica gel (EtOAc) and the product was recrystallized from diichloromethane/hexanes to yield 2.75 g (47%) of a solid, melting point 208° C.

Provenance & Evidence