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15.3.1.1.1.3.1.2 Method 2: From (2-Acylaryl)amines

DOI: 10.1055/sos-SD-015-00689

Larsen, R. D.; Cai, D.Science of Synthesis, (200515397.

The Vilsmeier reagent reacts with (2-acylaryl)amines 34, as the free amine or acetamide, to form 4-chloroquinolines.[‌81‌,‌82‌] With the acetanilides, higher yields are obtained. From 2-aminoacetophenones 34 (R2=H) the quinoline-3-carbaldehyde 36 is produced by bis-formylation (see intermediate 35) of the methyl ketone (Scheme 14). For substituted acetophenones 34 (R2=Me, Et), the 3-alkyl-4-chloroquinolines 37 are formed.[‌81‌,‌82‌]

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