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10.13.4.1.1.2.1.2 Method 2: From o-Aminoaryl Halomethyl Ketones; Sugasawa Indoxyl Synthesis

DOI: 10.1055/sos-SD-010-00559

Joule, J. A.Science of Synthesis, (200110621.

The ability to C-acylate anilines regioselectively ortho to the nitrogen (see also Section 10.13.1.1.1.2.1.7) permits the synthesis of o-(chloroacetyl)arylamines 1220 directly from the arylamine. It is a simple matter to bring about the intramolecular displacement of the halide by the amino group and thus provide one of the best ways in which to synthesize 1,2-dihydro-3H-indol-3-ones (indoxyls) 1221 (Scheme 452).[‌317‌] Sodium hydride at 0°C effects ring closure of the o-(chloroacetyl)arylamines, and potassium carbonate suffices with N-trifluoroacetyl o-(chloroacetyl)arylamines.

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