Quinoline sulfonation

The rate effects imposed by this derivative, however, are dependent on the structure of the substrate. For example, the hydrolysis of 8-acetoxy-5-quinoline-sulfonate (AQS), a large substrate which cannot be included within the cyclohexaamylose cavity, is not enhanced by this derivative. Moreover, in contrast to the effects of unmodified cycloamyloses on the hydrolyses of nitrophenyl acetates, the rate accelerations imposed by this... 

Keywords Alkyl hydroperoxides Amination Ammonia Benzimidazole Benzisoxazole Carbanions Heterocycles Hydroxylation Indole Nitro compounds Nucleophiles Nucleophilic substitution Oxidation Phenazine Potassium permanganate Pyridine Quinoline Sulfones Vicarious... 

QUINOLINES AND ISOQUINOLINES] (Vol 20) -ofapigment [PIGBffiNTS - ORGANIC] (Vol 19) -lignosulfates as [SULFONIC ACIDS] (Vol 23)... 

Sulfonation. The main sulfonation product of quinoline at 220°C is 8-quinoHnesulfonic acid [85-48-3]-, at 300°C it rearranges to 6-quinolinesulfonic acid [65433-95-6] (10). Optimum conditions for sulfonation, 2 h at 140°C and a 1 4 quinoline/40% (wt) oleum ratio, produces 80% yield. The yield drops to 64% at 130°C with a 1 3 reactant ratio (11). Somewhat higher, but variable, yields of 8-quinoHnesulfonic acid hydrochloride [85-48-3] have been reported with chlorosulfonic acid (12). 

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). 

The 8-hydroxy-7-aminoquinoline-5-sulfonic acid was used to clarify the role of intramolecular hydrogen bonding on the cyclization rate of hydroxy Schiff bases in the preparation of 2-aryloxazolo[4,5-/i]quinoline-5-sulfonic acids 13. Irradiation... 

Quinoline-5-sulfonic acid, 8-hydroxy-7-iodo-metal complexes absorptiometry, 1,549 Quinolinium salts in gravimetry, 1, 535 Quinolinol metal complexes color photography, 6,107 8-Quinolinol biological activity, 6, 771 gallium and indium complexes radiopharmacology, 6, 971 radionuclide complexes radiopharmacology, 6,994 8-Quinolyl sulfate hydrolysis metal catalysis, 6,465 Quinones... 

Nitro-, 4-nitro-, 7-nitro-, 5,7-dinitro-, and 6,8-dinitroquinoline react with the carbanion of chloromethyl phenyl sulfone to give products of substitution of hydrogen at positions 4 3 8 6,8 and 5,7 respectively <96LA641>. The base-induced reaction of benzoyl chloride salts of quinoline iV-oxides with carbonitriles to give 2-quinolyldiacylamines as the main products has been reported <96TL(37)69>. 

Quinoline yellow (E 104, Cl Food Yellow 13) is a quinophthalone dye consisting of a mixture of disulfonates (minimum 80%), monosulfonates (maximum 15%), and trisulfonates (maximum 7%) as sodium salts, obtained by the sulfonation of 2-(2-quinolyl)-l,3-indandione. The calcium and potassium salts are also permitted. Quinoline yellow is a yellow powder or granules, soluble in water, sparingly soluble in ethanol. The absorption maximum is at 411 nm in aqueous acetic acid solution, pH 5, = 865. It is not permitted as food colorant in the US. "... 

A bacterial strain BN6 oxidizes 5-aminonaphthalene-2-sulfonate by established pathways to 6-amino-2-hydroxybenzalpyruvate that undergoes spontaneous cyclization to 5-hydroxy-quinoline-2-carboxylate (Figure 2.2a) (Nortemann et al. 1993). 

Each of the three decahydroquinoline sulfonates shown below gives a different product composition on solvolysis. One gives 9-methylamino-E-non-5-enal, one gives 9-methylamino-Z-non-5-enal, and one gives a mixture of the two quinoline derivatives 14-D and 14-E. Deduce which compound gives rise to which product. Explain your reasoning. 

Triphenylmethane leuco dyes are used for photographic materials. The photographic system requires a polymer binder such as acrylic acid-methyl methacrylate copolymer115 or a copolymer of isophthalic and terephthalic acids116 a sensitizer such as 4-(4-n-amyloxyphenyl)-2,6-bis(3-ethylphenyl)-thiapyrilium perchlorate,117 a photo initiator such as hexaarylbisimi-dazole,118 and phenyl tribromomethyl sulfone, cycloalkane such as 1,2,3, 4,5-pentabromo-6-chlorocyclohexane,119 or 3-benzylidene-9-methyl-2,3-dihydro- 1 TZ-cyclopenta [b] quinoline.120... 

Abou-Ouf et al. [16] described a spectrophotometric method for the determination of primaquine phosphate in pharmaceutical preparation. Two color reactions for the analysis of primaquine phosphate dosage form, which are based on 2,6-dichlor-oquinone chlorimide and l,2-naphthoquinone-4-sulfonate, were described. The reactions depend on the presence of active centers in the primaquine molecule. These are the hydrogen atoms at position 5 of the quinoline nucleus and the primary amino group of the side chain. The method was applied to tablets of primaquine phosphate and a combination of primaquine phosphate and amodiaquine hydrochloride. 

Zhujun Z., Seitz W.R., A fluorescent sensor for aluminum(III), magnesium(II), zinc(II) and cadmium(II) based on electrostatically immobilized quinolin-8-ol sulfonate. Anal. 

E. Jacobson in 1882 fused phthalic anhydride with quinoline bases obtained from coal tar, which also contained quinaldine (136). He thus received quinophthalone (137). Quinophthalone derivatives bearing sulfonic or carboxylic acid functions represent suitable anionic dyes. Derivatives carrying basic side chains containing quarternary nitrogen, on the other hand, provide cationic dyes. The compounds are used especially as disperse dyes [1]. 

There are many interesting derivatives of quinoline and acridine obtained by substitution. In particular, 8-hydroxyquinoline (oxine) is the second complexing agent in importance after EDTA. Sulfonation in position 5 leads to a compound which is soluble in water and that exhibits outstanding fluorogenic properties (i.e. fluorescence enhancement) on complexation with metal ions (e.g. aluminum). 

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