[N:1]1([C:11]2[CH2:16][CH2:15][CH2:14][C:13](=[O:17])[CH:12]=2)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][CH2:2]1.O>CN(C=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH:8]1[CH:7]=[CH:6][C:5]2[CH2:4][CH2:3][CH2:2][N:1]3[C:10]=2[C:9]=1[C:12]1[C:13](=[O:17])[CH2:14][CH2:15][CH2:16][C:11]=13Cupric acetate (878 mg) was added to a solution of 3-(1,2,3,4-tetrahydro-1-quinolinyl)-2-cyclohexen-1-one (500 mg) and palladium (II) acetate (100 mg) in dry DMF (10 ml). The mixture was heated at 135° under nitrogen for 3 h, cooled, poured into water (100 ml) and extracted with ethyl acetate (4×50 ml). The combined, dried organic extracts were evaporated to give a solid (ca. 490 mg) which was purified by FCC eluting with ethyl acetate:hexane (2:1) to give the title compound (285 mg), m.p. 160°-164°.
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