Quinoline 3-amino-4-nitro

Method of Nys and Rekker The Nys and Rekker method [53,54] has been developed for mono- and di-substituted benzenes. The substituents considered are halogen atoms and hydroxyl, ether, amino, nitro, and carboxyl groups, for which contributions have been calculated by multiple regression analysis (s = 0.106, r = 0.994, F = 1405). Rekker discusses the extension of his approach to other compound classes, such as PAHs, pyridines, quinolines, and isoquinolines. 

Corrosion Inhibitors. Steel-reinforcing wire and rods embedded in concrete containing quinoline or quinoline chromate are less susceptible to corrosion (72) (see Corrosion and corrosion control). Treating the surface of metals with 8-hydroxyquinoline [148-24-3] makes them resistant to tarnishing and corrosion (73). Ethylene glycol-type antifreeze may contain quinoline, 2-chloro-, 4-amino-, 8-nitro-, or 8-hydroxyquinoline to prevent corrosion (74). 

A solution of N-(2-aminobenzvl)-1-phenyl-2-metKylaminoethanol-1 was prepared by the reaction of a-bromo-acetophenone and (2-nitrobenzyl)methylamine, followed by hydrogenation of the nitro group by means of nickei on diatomaceous earth at room temperature and reduction of the CO group by means of sodium borohydride. The intermediate thus produced was dissolved in 100 ml of methylene chloride and introduced dropwise into 125 ml of sulfuric acid at 10° to 15°C. After a short standing, the reaction mixture was poured onto ice and rendered alkaline by means of a sodium hydroxide solution. Dy extraction with ether, there was obtained 1,2,3,4-tetrahydro-2-methyl-4-phenyl-8-amino-iso-quinoline. The base is reacted with maleic acid to give the maleate melting point of the maleate 199° to 201°C (from ethanol). 

The reduction of aromatic nitro compounds to amino derivatives and cyclizations to various heterocyclic compounds are presented in Chapter 9. Recent advances are presented here. Reaction of 2-nitrobenzaldehyde with vinyl carbonyl compounds in the presence of 1,4-diazbi-cyclo[2.2.2]octane affords Baylis-Hillman products, the catalytic reduction of which results in direct cyclization to quinoline derivatives (Eq. 10.78).134... 

Piperidines have often been prepared by condensation between suitably placed primary amino and carbonyl groups. The simplest cases would be 5-aminopentanals or the corresponding ketones, and the common approach to these is from the nitro compounds by reduction. Syntheses of 3-hydroxypiperidines follow this route (equation 4) (74BSF1001). A number of quinoline syntheses involve the reduction of an o-nitrocinnamyl derivative the simplest uses o-nitrocinnamaldehyde. Potassium tetracarbonylhydridoferrate reduces (5) to quinoline in quantitative yield. If more vigorous reduction is required the aldehyde... 

The oxidising agent usually employed is the nitro-compound corresponding to the amine, e.g., nitrobenzene when aniline is the base for p-toluidine, p-nitrotoluene serves, and so on. Arsenic acid, however, can be generally employed, and gives better results. The reaction is capable of very wide application nitro-, halogen-, hydroxy-, carboxy-quinolines can all be obtained from the corresponding amines the amino-naphthalenes also react. Diamines yield the so-called phen-anthrolines. (B., 16, 2519 23, 1016.)... 

Vilsmeier reaction, 4, 1051 Furo[3,2-6]pyrroles MO calculations, 6, 979 synthesis, 4, 1069 6, 1009 Furo[3,4-a]pyrrolo[2,1,5-cd]indolizine nomenclature, 1, 22 Furopyrylium salts, 4, 993-995 Furoquinolines biosynthesis, 4, 992 occurrence, 4, 988 pharmacology, 4, 992 reactions, 4, 988 synthesis, 4, 989 Furo[3,2-c]quinolines, 4, 991 Furo[3,4-fe]quinoxaline, 1,3-diphenyl-synthesis, 4, 993 Furoquinoxalines, 4, 992 Furo[2,3-6]quinoxalines synthesis, 4, 992 Furosemide toxicity, 1, 136 Furospinulosin UV spectra, 4, 587 Furospongin-I mass spectrometry, 4, 583 Furo[3,4-d][l,2,3]triazole, 2,6-dihydro-synthesis, 6, 996 Furo[3,4 -d][ 1,2,3]triazoles synthesis, 6, 996 Furoxan, 4-amino-3-aryl-tautomerism, 6, 404 Furoxan, 4-amino-3-methyl-synthesis, 4, 414 Furoxan, 4-aryl-3-methyl-rearrangement, 6, 408 Furoxan, 3-aryl-4-nitro-synthesis, 6, 414 Furoxan, 4-benzoyl-3-methyl-oxime... 

Baughman (1992) measured the disappearance rate constants for a number of solvent and disperse azo, anthraquinone, and quinoline dyes in anaerobic sediments. The half-lives ranged from 0.1 to 140 days. Product studies of the azo dyes showed that reduction of the azo linkages and nitro groups resulted in the formation of substituted anilines. The 1,4-diaminoanthraquinone dyes underwent complex reactions thought to involve reduction and replacement of amino with hydroxy groups. Demethylation of methoxyanthraquinone dyes and reduction of anthraquinone dyes to anthrones also was observed. 

The cyclization of orr/io-diazonium hydrazones provides a regioselective synthesis of A-amino-triazolopyridines (Scheme 38 and Equations (22)-(24)). Thus, 3-amino-4-(benzylidenehydrazino) pyridine (192), 3-amino-2-(benzylidenehydrazino)pyridine (193), 3-nitro-4-(benzylidenehydrazino) quinoline (194), and 3-amino-2-(benzylidenehydrazino)quinoline (195) afforded 1-amino-triazolo[4,5-c]pyridine (197), 3-aminotriazolo[4,5-6]pyridine (198), l-aminotriazolo[4,5-c]quinoline (199), and 3-aminotriazolo[4,5-6]quinoline (200), respectively <69JCS(C)1758>. 

---