0 Hits

  • Previous / Next

You are using Science Of Synthesis as a Guest.
Please login to access the full content or check if you have access via 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]

Meeeee 88 Meeeeeee ee 8-Meeeeeeeeeeeee eeee eee Meeeeeeee Meeeeee[‌88‌,‌88‌]

Meeeeeeeeeee Meeeeeeee

8-Meeeee-8-eeeeeeeeeeeeeee (88, M8=Me; M8=M); Meeeeee Meeeeeeee:[‌88‌]

Me e eeeeeee eeee ee M-[8-(8-eeeeeeeee)eeeeee]eeeeeeeee (88, M8=Me; M8=Me; M8=M; 8.888e, 8.8eeee) ee MMM (8.888e, 88eeee), eeeeee ee 8°M, MMMe8 (8.88e, 88eeee) eee eeeee eeeeeeee eeee 88eee. Mee eeeeeee eee eeeeeee ee ee eee 8e eee eeeeeeeeee ee 88°M eee 8e. Mee eeeeeeeee eeeeeee eee eeeeeeeeeee eeee eeeeeee eee eeeeeeeeee MeMMe, eee eeee eeeeeeeee. Mee eeeeee eeee eeeeeeeee, eeeeeeee, eee eeeeeeee ee eeeeee eeeeeeeeeeeeee (eeeeeeeee eeeee/MeMMe 8:8) ee eeeee eee eeeeeeeee; eeeee: 8.88e (88%); ee 88°M.