[CH:1]1([NH:11][CH:12]=[O:13])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][CH2:2]1.Br.[O:15]=O.[Cl-].[Na+]>C(O)(=O)C.O.C(C(C)=O)C(C)C>[O:15]=[C:4]1[C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[CH:1]([NH:11][CH:12]=[O:13])[CH2:2][CH2:3]1A mixture of N-(1,2,3,4-tetrahydro-1-naphthyl)-formamide (2.0 g), cobaltous acetate tetrahydrate (0.95 g), a 30% solution of hydrobromic acid in acetic acid (0.925 g) and a 1:1 mixture of acetic acid: methyl isobutyl ketone (40 ml) is stirred and oxygen introduced via a capillary gas delivery tube. The blue reaction mixture is gradually heated to 76° C. in 42 minutes during which time the color changes to purple. The reaction mixture is then allowed to cool to room temperature. Water (40 ml) is added and the mixture saturated with sodium chloride. The mixture is extracted with chloroform (3×20 ml), the combined extracts are washed with saturated sodium chloride solution, dried over anhydrous magnesium sulfate and evaporated to dryness in vacuo. The residual red oil is triturated with ether and after cooling the title compound (0.4 g) collected. Further work-up of the mother liquor affords an additional 0.6 g of title compound.
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