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Please login to access the full content or check if you have access via Variation 3: Reilly–Hickinbottom and Orton Rearrangements

DOI: 10.1055/sos-SD-040-00241

Purchase, R.; Sainsbury, M.Science of Synthesis, (200940391.

A seemingly related reaction is known as the ReillyHickinbottom rearrangement in which an alkyl(aryl)amine is heated at 200350°C with a metal halide, phosgene, cadmium(II) chloride, or zinc(II) chloride to give a C-alkylated aniline.[‌138‌] In much the same way N-chloro-N-phenylacetamide (134), when treated with hydrochloric acid, affords N-(4-chlorophenyl)acetamide (135) by a process known as the Orton rearrangement (Scheme 38).[‌139‌‌142‌] However, in this case there is evidence that when N-chloro- or N-bromobenzamides are exposed to an acid in an aprotic solvent the corresponding 4-halobenzamides are produced by an intramolecular mechanism that utilizes ion pairs.[‌143‌]

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