1,4-Naphthoquinone → 5,14-Dihydro-7-phenylbenz[5,6]isoindolo[2,1-b]isoquinoline-8,13-dione

Participants

Reaction Conditions

Reaction Steps

A mixture of 2-benzoyl-1,2,3,4-tetrahydro-3-isoquinoline carboxylic acid (6.0 g) and 1,4-naphthalenedione (6.75 g) in acetic anhydride (240 ml) was stirred at about 100° C. for 20 minutes. The reaction mixture was allowed to stand at room temperature for 48 hours, and the green solid (7.16 g) was collected by filtration. The crude product was recrystallised from chloroform-petroleum ether (b.b. 40°-60° C.) to give the title compound (5.04 g) m.p. 267° C. (decomp), λmax (in ethanol) 246.5 nm (ε45,500), 320 nm (ε2,440), 388 nm (ε6,120).

Provenance & Evidence