Ethanol → 9-(4-Chlorophenyl)-3,4,5,6,7,8,9,10-octahydro-1(2H)-acridinone

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Reaction Steps

To a stirred 70° C. mixture of 9-(4-chlorophenyl)-3,4,6,7,9,10-hexahydro-1,8(2H,5H)-acridinedione (6.0 g), ethanol (160 mL) and pyridine (50 mL) was added sodium borohydride (7.5 g, 198.4 mmole) in two portions over six hours. The solvent was removed; the resulting yellow solid washed well with water and dried in vacuo. Chromatography (methylene chloride/ethyl acetate; 85/15) and recrystallization from ethanol provided the title compound (1.0 g) as a white solid, mp 253°-254° C.; NMR: 1.41-1.51 (m,3, CH2), 1.60-1.88 (m,5, CH2), 2.07-2.14 (m,4, CH2), 2.38-2.41 (m,2, CH2), 4.16 (s,1, CH), 7.16 (d,2, J=8.4, Ar), 7.25 (d,2, J=8.4, Ar), 8.39 (s,1, NH); (CI, CH4) MS: m/z=314(M+1). Analysis for C19H20ClNO: Calculated: C, 72.72; H, 6.37; N, 4.46; Found: C, 72.35; H, 6.60; N, 4.29.

Provenance & Evidence