Ethanol → 9-(3-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-(3-chlorophenyl)-3,4,6,7,9,10-hexahydro-1,8(2H,5H)-acridinedione (5.0 g), ethanol (120 mL) and pyridine (40 mL) was added sodium borohydride (7.5 g) in two portions over six hours. The solvent was removed; the resulting yellow solid washed well with water and dried in vacuo to provide the title compound (5.0 g) as a yellow solid. Recrystallization from ethanol returned analytically pure material, mp 249°-250° C.; NMR: 1.41-1.51 (m,3, CH2), 1.60-1.88 (m,5, CH2), 2.09-2.15 (m,4, CH2), 2.39-2.45 (m,2, CH2), 4.17 (s,1, CH), 7.09-7.15 (m,3, Ar), 7.21-7.26 (m,1, Ar), 8.43 (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, 72.55; H, 6.48; N, 4.49.

Provenance & Evidence