Friedlander synthesis

Quinoline synthesis from the condensation of o-aminobenzaldehyde with aldehyde or ketone in the presence of NaOH. 

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Friedlander synthesis, 2, 445 Acridine-1,8-diones, hexahydro-synthesis, 2, 482 Acridine Orange colour and constitution, 1, 346 nucleic acid stain, 1, 179... 

Friedlander synthesis, 2, 445 Benz[c]acri dines synthesis, 2, 441... 

Friedlander synthesis, 2, 444 Benzacridinones, dihydro-von Niementowski synthesis, 2, 447 Benz[6]acridinones, tetrahydro-von Niementowski synthesis, 2, 447 Benzaldehyde... 

Free Electron Molecular Orbital method colour and constitution, 1, 342 Freelingyne occurrence, 4, 706 Free radical processes in photography, 1, 387-389 Friedlander synthesis quinolines, 2, 443 thioindigo dyes, 4, 910 Fries rearrangement chroman-4-one synthesis from, 3, 850 Fructose, 1-deoxy- C NMR, 4, 575 Frusemide as diuretic, 1, 174 metabolism, 1, 245 FS-32 — see 1/f-Indazole, l-[3-... 

Furan-2-carbaldehyde, 3-amino-Friedlander synthesis, 4, 648 Furan-2-carbaldehyde, 3-azido-reduction, 4, 647 Furan-2-carbaldehyde, 4-bromo-X-ray diffraction, 4, 543 Furan-2-carbaldehyde, 5-bromo-nucleophilic substitution, 4, 612 reactions... 

Friedlander synthesis, 2, 445 Quinoline, alkenyl-1,2-dihydro-disproportionation, 2, 369 Quinoline, 2-alkoxy-reactions, 2, 351 Quinoline, 4-alkoxy-reactions, 2, 351 Quinoline, 2-alkoxy-4-hydroxy-synthesis... 

Friedlander synthesis, 2, 444 Quinoline, 2-aryl-4-phenyl-synthesis... 

Friedlander synthesis, 2, 443 Quinoline, perhydro-conformation, 2, 160 synthesis, 2, 376 Quinoline, 2-phenyl-reactions... 

Friedlander synthesis, 2, 444 as antipyretic, 1, 172 Quinoline-4-carboxylic acids amination, 2, 236 Beyer synthesis, 2, 475 Pfitzinger synthesis, 2, 446... 

Beyer synthesis, 2, 474 electrolytic oxidation, 2, 325 7r-electron density calculations, 2, 316 1-electron reduction, 2, 282, 283 electrophilic halogenation, 2, 49 electrophilic substitution, 2, 49 Emmert reaction, 2, 276 food preservative, 1,411 free radical acylation, 2, 298 free radical alkylation, 2, 45, 295 free radical amidation, 2, 299 free radical arylation, 2, 295 Friedel-Crafts reactions, 2, 208 Friedlander synthesis, 2, 70, 443 fluorination, 2, 199 halogenation, 2, 40 hydrogenation, 2, 45, 284-285, 327 hydrogen-deuterium exchange, 2, 196, 286 hydroxylation, 2, 325 iodination, 2, 202, 320 ionization constants, 2, 172 IR spectra, 2, 18 lithiation, 2, 267... 

In this method the nitro group in the aliphatic nitro compound is usually present on a carbon atom, which is also activated by CO-functioiiality (aldehyde, ester, arylketoiie). A successful application of this method is the Borsche modification of the Friedlander synthesis, involving condensation of A-(3-amino-4-picolylidene)-p-toluidine (17) with [Pg.289]

The mechanistic pathway of the ordinary Friedlander synthesis is not rigorously known. Two steps are formulated. In a first step a condensation reaction, catalyzed by acid or base, takes place, that can lead to formation of two different types of products (a) an imine (Schiff base) 4, or (b) an o ,/3-unsaturated carbonyl compound 5 ... 

Friedlander synthesis org chem A synthesis of quinolines the method is usually catalyzed by bases and consists of condensation of an aromatic p-amino-carbonyl derivative with a compound containing a methylene group in the alpha position to the carbonyl. fred.lan dar. sin-tha-sas ... 

Another approach, the Friedlander synthesis, is to condense a 2-aminophenyl ketone with an aldehyde or ketone that contains a methylene unit (to permit enolization and subsequent aromatization), in contact with either an acid or a base as the catalyst (Scheme 3.8). 

Other pyridine-forming reactions of this class bear some resemblance to the Friedlander synthesis and its near relations. The enamino ketones (328) condense with 1,3-diketones... 

The most important synthesis in this class is that of quinolines, due to Friedlander, with its major modifications by Pfitzinger and by von Niementowski. The Friedlander synthesis has been comprehensively reviewed (77HC(32-1)181, 820R(28)37, 80T2359), the last two reviews dealing only with the true Friedlander procedure. This is exemplified in equation (52), and the various possible modifications are indicated by the substituents. 

A reaction which formally resembles a Friedlander synthesis is that between o-aminobenz-aldehyde and iodobenzene, the resulting 2-formyldiphenylamine being cyclized by acid to give acridine (17CB1306). Quinolines (372) can be synthesized by passing mixtures of o-nitrobenzaldehyde and alcohols over a Cu-Ni-V205 catalyst at 300-320 °C (76MI20801). 

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