Hydrogenation of 1,8-Naphthalenedicarboximide and Its Derivatives over Palladium Catalys

Abstract

Catalytic hydrogenation of 1,8-naphthalenedicarboximide [1 a] and 4-substituted-N-methyl-1,8-naphthalenedicarboximides [1 b~f] (X = H, OCH3, OH,NH2, SO2Na) over palladium catalyst has been studied. First, [1 a] was hydrogenated (80°C and 50 kg/cm2 of initial hydrogen pressure) to give 1,2,3,4-tetrahydro-l, 8-naphthalenedicarboximide [2 a] (in 77% yield). The activity of palladium catalyst for the hydrogenation was higher than those of other plutinum group catalysts (Ru, Rh, and Pt). The hydrogenation of [l a] under more drastic conditions (250°C and 50 kg/cm2 of initial hydrogen pressure) gave decalin-1,8-dicarboximide [3]. Next, [1 b~e] were hydrogenated (85, 225, 150, 220°C and 50, 80, 70, 80 kg/cm2 of initial hydrogen pressure) to give the corresponding 5-substituted-N-methyl-l, 2,3,4-tetrahydro-l, 8-naphthalenedicarboximides [2 b~e] (in 60~80% yields). But [1 f] gave [l b], because the ring hydrogenation did not occur under the same conditions. Acetylation of [2a] and [2b] with acetyl chloride gave 3-acetoxy-5,6-dihydro-4 H-benz[de] isoquinolin-1-one [4 a] and 3-acetoxy-2-methyl-5,6-dihydro-4 H-benz[de]isoquinolin-l-one [4 b], respectively. © 1978, The Chemical Society of Japan. All rights reserved.