Synthesis of Anthranilonitriles by Fragmentation of Isatin Oxime Triflates

References

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• For general experimental details, see following paper.
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• 7-Bromoisatin was synthesized according to the procedure of Marvel, et. al. described in reference 4a. The product was obtained as an orange solid (59% yield over two steps), mp, 212–214°C. CAUTION! The procedure described by Marvel, et. al., generates small, but potentially hazardous, levels of HCN. See Goodwin, B.; and Candy R.; Hill H. G. in Chemistry in Britain, 1988, 336. The 7-bromoisatin oxime was prepared by heating the isatin together with hydroxylamine hydrochloride in aqueous ethanol. A yellow solid was recovered (952 yield), mp, >250°C.
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• In most cases the mixture must he heated to drive the reaction at an appreciable rate. A factor which limited the reaction rate was the poor solubility of the isatin oxime in CH2Cl2 and most other solvents compatible with the reagents.
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