Following a close literature precedent in Bioorg. Med. Chem. Lett. 15, 2005, 4867-71, I was trying to make an intermediate piece from a substituted nitroaniline using Bartoli indole synthesis [J. Chem. Soc. Perkin 2, 1991, 657-663]. I got some indole alright. The yields are average of two runs at one gram scale, workup was done with sat NH4Cl. I think this qualifies in the “Look what happened to me doc – it’s all black” category.