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Larsen, R. D.; Cai, D., Science of Synthesis, (2005) 15, 397.
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; 8.888 e, 8.8 eeee) ee MMM (8.888 e, 88 eeee), eeeeee ee 8°M, MMMe8 (8.88 e, 88 eeee) eee eeeee eeeeeeee eeee 88 eee. Mee eeeeeee eee eeeeeee ee ee eee 8 e eee eeeeeeeeee ee 88°M eee 8 e. 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: 8.88 e (88%); ee 88°M.
References
| [81] | Meeeeee, M. M.; Meeeeee, M. M., Meeeee M. Meee., Meee. M, (8888) 88, 888. |
| [82] | Meeeeee, M. M.; Meeeeee, M. M., Meeee. Meeeee., (8888) 88, 888. |
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