Doebner-von Miller synthesis

By substituting paraldehyde for glycerol, 2-methylquinoline [27601-00-9] may be synthesized. The Skraup synthesis is regarded as an example of the broader Doebner-von Miller synthesis. In the case of the Skraup synthesis, the glycerol undergoes an acid-catalyzed dehydration to provide a small concentration of acrolein that is the reactive species. If acrolein itself is used as a reactant, it would polymerize. Crotonaldehyde is the reactive intermediate in the Doebner-von Miller synthesis (28). 

Doebner-von Miller synthesis, 2, 466 hydrazination, 2, 238 NMR, 2, 120 Quinoline, 5-methyl-nitration, 2, 50, 318 Quinoline, 6-methyl-mercuration, 2, 321 N-oxide... 

Quinoline, 2-(N-methylcarboxamido)-conformation, 2, 111 Quinoline, 2-methyl-1,2-dihydro-Doebner-von Miller synthesis, 2, 466 Quinoline, 2-methyl-2,4-diphenyl-1,2-dihydro-synthesis, 2, 476... 

Doebner-von Miller synthesis, 2, 466 synthesis, 2, 318 Quinoline, 3-pentyl-... 

Quinoline, 2,2,4-trimethyl-1,2-dihydro-antioxidant in polymers, 1, 395 Doebner-von Miller synthesis, 2, 468 Quinoline, trimethylstannyl-reactions, 2, 364 Quinoline, 4-vinyl-polymers, 1, 286... 

Dodecylphenol (PDDP), 2 222—223 health and safety data, 2 220t physical properties of, 2 205t Dodecylsuccinic anhydride (DDSA), 10 406 Doebner-von Miller synthesis, 2 787 DOE Pro XL 3.0, features compared to other software, 8 398t Dofetilide, 5 102, 104, 106... 

In the original Doebner-von Miller synthesis of quinolines an arylamine condenses with two molecules of an aldehyde most of the variants have been dealt with in Section 2.08.2.2.3.ii since the intermediate (often used directly) is an a,-unsaturated aldehyde. Two further major variations, the Beyer modification and the Doebner cinchoninic acid synthesis, will be dealt with here, since intermediates are rarely isolated. 

Quinoline, 5-nitro-oxidation, 2, 210 synthesis, 2, 318 Quinoline, 6-nitro-nitration, 2, 318 Quinoline, 7-nitro-nitration, 2, 318 synthesis, 2, 318 Quinoline, 8-nitro-Doebner-von Miller synthesis, 2, 466 synthesis, 2, 318 Quinoline, 3-pentyl-Friedlander synthesis, 2, 443 Quinoline, perhydro-conformation, 2, 160 synthesis, 2, 376 Quinoline, 2-phenyl-reactions... 

The Skraup-Doebner-Von Miller synthesis of quinolines - involving condensation of an aniline with an ,/i-unsalurated ketone - has been investigated using 13C-labelled ketones in cross-over experiments a complex fragmentation-recombination mechanism involving imine intermediates is indicated.17... 

Problem 31.26 Account for the formation of 2,4-dimethyIquinoline from aniline and acetylacetone (2,4-pentanedione) by the Doebner-von Miller synthesis. 

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