7- Bromo-4- quinoline

Quinoline, 2,4-bis(dimethylamino)-synthesis, 2, 419, 469 Quinoline, 3-bromo-bromination, 2, 319 oxidation, 2, 325 Skraup synthesis, 2, 467 Quinoline, 5-bromo-bromination, 2, 319 nucleophilic substitution, 2, 324 Quinoline, 6-bromo-nucleophilic substitution, 2, 324 Quinoline, 8-bromo-bromination, 2, 319 N-oxide... 

Two simple applications may be mentioned. With cyciohexene (I) 3-bromo-cycZohexene (II) is obtained in good yield the latter upon dehydrobromlnation with quinoline affords an 80-90 per cent, yield of 1 3-cycfohexadiene (III) ... 

This mixture is known as Quinoline Yellow A [8003-22-3] (Cl 47000) and is most widely used with polyester fibers (109). Upon sulfonation, the water-soluble Quinoline Yellow S or Acid Yellow 3 [8004-92-0] (Cl 47005) is obtained. This dye is used with wool and its aluminum salt as a pigment. Foron Yellow SE-3GL (Cl Disperse Yellow 64) is the 3-hydroxy-4-bromo derivative. Several other quinoline dyes are commercially available and find apphcations as biological stains and analytical reagents (110). 

Ubichromenol synthesis, 3, 752 Ugi reaction, 5, 830 Uliginosin B, bromo-molecular dimensions, 3, 621 Ullman and Fetvadjian synthesis quinolines, 2, 477 Ullman synthesis acridines, 2, 470-benzacridines, 2, 470 Ultraviolet light absorbers in polymers, 1, 397-398 Ultraviolet spectroscopy heterocyclic compounds reviews, 1, 78... 

Halothiophenes, which are not activated through the presence of —I—M-substituents, undergo substitution smoothly under more forcing conditions with copper salts in pyridine or quinoline. Hence 3-cyanothiophene and 5-methyl-2-cyanothiophene have been obtained from the corresponding bromo compounds. 2-Bromothiophene reacts readily with aliphatic cuprous mercaptides in quinoline at 200°C to give thioethers in high yields. The use of the copper-catalyzed Williamson synthesis of alkoxythiophenes from iodo- or bromo-thiophenes and alcoholate has been mentioned before. The reaction of 2-bromothiophene with acetanilide in nitrobenzene in... 

Pyridyne (26) has been shown to exist by trapping it with furan. It must be considered to be an intermediate in the reaction of 3-bromo-2-chloropyridine (49) with lithium amalgam because in the presence of furan a small amount (2%) of quinoline (50) is formed. ... 

Quinolynes are generated and behave analogously to pyridynes. The reaction of 3-bromo-4-chloro- and 3-bromo-2-chloro-quinoline with lithium amalgam in the presence of furan gives phenanthridine (83, 9% yield) and acridine (85, 0.1% yield), respectively, via 3,4-... 

In an extensive investigation of the behavior of halogeno-pyridines and -quinolines towards potassium amide in liquid ammonia, tendencies to react according to the hetaryne type and other mechanisms were compared. The following results may be mentioned. 3-Fluoropyridine does not react via 3,4-pyridyne, but yields fluoro derivatives of 4,4 - and 2,4 -bipyridine. 3,6-Dibromopyridine is converted first into 6-bromo-3,4-pyridyne and not into 6-amino-3-bromopyridine. 2-Bromoquinoline yields 2-methylquinazoline together with 2-aminoquinohne. ... 

As summarized in the following tabulation, the relative rates of piperidino-debromination of the halo-l-nitronaphtholenes (data from Table XII, numbered to show relation to quinolines) provide a good confirmation of the relation of induction (ind.) to resonance activation (res.) and of the extent of transmission of activation to an adjoining ring. Here again, as in the quinoline series, the 8-isomer (346) is more reactive than its resonance-activated 5-bromo isomer (345) and its inductively activated 3- and 6-bromo isomers (351 and... 

Bromoisoquinoline can be aminated under vigorous conditions (concentrated NH4OH, 165°, 16 hr), - but attempted methoxyla-tion (methanolic methoxide, 235°, 7 hr) gave isoquinoline (50% yield) via the reductive reaction observed with 6- and 8-bromo-quinoline. ... 

The dinitro derivative of compound 2 reacts with anhydro bases of pyridine and quinoline to give zwitterions such as 215 (99RCB1391). Compound 216 has been made from the 3-bromo derivative of compound 3 by reaction with an amine, as an intermediate in the production of stomach secretion inhibitors (80EUP48555),... 

Bromination of the diphenyl indole derivative 316 with bromine in DMF or trimethylammonium bromide afforded the 7-bromo derivative 317. Reaction with allyl bromide or its derivatives gave A-allyl derivatives 318 that upon cyclization with palladium acetate gave 7,9-dimethoxy-l,2-diphenylpyrrolo[3,2,l-// ]quinoline derivatives 319 (92T7601) (Scheme 57). 

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). 

Bromination. Neutral bromination of quinoline (66) using bromine in hot carbon tetrachloride and pyridine gave the 3-bromo derivative (68) (90%) and 3,6-dibromoquinoline (69) (2%), along with traces of 3,8-di-and 3,6,8-tri-bromo products [59CI(L) 1449 66AHC(7)1]. There is some... 

Bromine in acetic acid readily converted the activated 3-hydroxy-quinoline into its 4-bromo derivative (76%) under similar conditions 8-hydroxyquinoline gave a mixture of the 5-bromo and 5,7-dibromo compounds [71BAU400 72JOC4078]. All of the possible monobromo derivatives of the latter substrate have been made (91M935). 4-Hydroxy-... 

Vapor phase brominations have given rise to varying products dependent on the reaction temperature. At 300°C bromine converted quinoline in the presence of pumice into 68 (25%) at 450°C 2-bromoquinoline (25%) became the major product at 500°C the yield of the 2-bromo isomer increased to 53%, but there was some dibrominated material [77HC(32-1)319]. The absence of 3-bromoquinoline at the higher temperatures could be accounted for in terms of radical attack, or it could be due to thermal instability of that isomer [59CI(L)1449]. 

Among the nucleophilic processes available for introduction of bromine to quinolines are reactions of the diazonium salts (87JHC181) and syntheses based on hydroxyquinolines or quinolones (91M935) (Scheme 36). The former processes are especially useful for making 5-, 6-, 7-, and 8-bromo derivatives. Halogen-halogen exchange reactions have also been reported, but they are not common. When perfluoroquinoline was heated... 

When position 6 on the 2-quinolone is blocked, bromination takes place selectively at the 3-position. Thus, microwave irradiation of 45 in acetonitrile at 150 °C for 50 min afforded the 3-bromo-quinolin-2(lff)-one 46 in 87% yield (Scheme 12). 

A novel route to indoles and quinolines has been developed by sequential Wiltig and Heck reactions <96CC2253>. Thus, treatment of o-bromo- or iodo-lV-lrifluoroaceiylanilines (86) with a stabilized phosphorane affords the corresponding enamines 87 as a mixture of isomers. Cyclization to 88 is effected by heating with palladium acetate, tri phenyl phosphine, and bu.se. 

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