Chloride Acridine

Ferric chloride Acridines from acridanes s. 1, 23, 756 2, 91/2 Potassium ferricyanide, mercuric oxide Suhst. oximes from subst. hydroxylamines s. 3, 403 FeCl,... 

In complex cases, the prefixes amino- and imino- may be changed to ammonio- and iminio- and are followed by the name of the molecule representing the most complex group attached to this nitrogen atom and are preceded by the names of the other radicals attached to this nitrogen. Finally the name of the anion is added separately. For example, the name might be 1-trimethylammonio-acridine chloride or 1-acridinyltrimethylammonium chloride. 

Acriflavin Mixture (Euflavin, 3,6-diamino-lO-metbylacridiniuni chloride) [8063-24-9] M 259.7, m 179-181 . Purified by dissolving in 50 parts of H2O, shake with a small excess of freshly ppted and washed Ag20. The mixture is set aside overnight at 0 and filtered. The cake is not washed. The pH of the filtrate is adjusted to 7.0 with HCl and evaporated to dryness. The residue is then crystd twice from MeOH, twice from H2O and dried at 120 X ,ax at 452nm has a loge value of 4.67. It is a red powder which readily absorbs H2O. The solubility is increased in the presence of proflavin. The dihydrochloride is a deep red crystn powder. It is available as a mixture of 3,6-diaminoacridinium chloride (35%) and its 10-metho-chloride (65%). [see Albert, The Acridines Arnold Press p. 346 1966 Chem Ber 45 1787 1912]. 

Kawabata Y., Tahara R., Imasaka T., Ishibashi N., Fiber-optic potassium ion sensor using alkyl-acridine orange in plasticized poly(vinyl chloride) membrane, Anal. Chem. 1990 62 1528. 

Several N-methyl-9-acridinecarboxylic acid derivatives (e.g., 10-methyl-9-acridinecarboxylic chloride and esters derived therefrom [39]) are chemiluminescent in alkaline aqueous solutions (but not in aprotic solvents). The emission is similar to that seen in the CL of lucigenin and the ultimate product of the reaction is N-methylacridone, leading to the conclusion that the lowest excited singlet state of N-methylacridone is the emitting species [40], In the case of the N-methyl-9-acridinecarboxylates the critical intermediate is believed to be either a linear peroxide [41, 42] or a dioxetanone [43, 44], Reduced acridines (acridanes) such as N-methyl-9-bis (alkoxy) methylacridan [45] also emit N-methylacridone-like CL when oxidized in alkaline, aqueous solutions. Presumably an early step in the oxidation process aromatizes the acridan ring. 

To a solution of oxalic chloride (5 g) in dichloromethane, a solution of diphenyl amine (5 g) in dichloromethane was added dropwise and refluxed for 30 min. The solution was concentrated (50%) and aluminum trichloride (8 g) added in portions. The mixture was refluxed for 45 min and the solvent evaporated. To this residue hydrochloric acid in ice water (1 M) was added and the red-colored precipitate filtered. The precipitate was dissolved in potassium hydroxide (10% in water), refluxed overnight, and poured into hydrochloric acid in ice water (5 M). The yellow acridine-9-carboxylic acid was filtered, washed with water, and dried. 

Acridine-9-carboxylic acid (1 g) was mixed with thionyl chloride (20 mL) and refluxed until a clear solution was obtained. The solution was concentrated and... 

Although chlorination, bromination and iodination of thiophenes by polyhalide salts require forcing conditions with the addition of zinc chloride [52], halogenation of acridine and acridone has been recorded to yield both 3-halo and 3,7-dihalo derivatives under relatively mild reaction conditions [53], However, whereas chloro-, bromo- and iodo-compounds are readily obtained from acridone, acridine only forms the bromo derivatives, as it produces stable complexes with the dichloroiodate and tetrachloroiodate salts [53]. 

Y. Kawabata, T. Kamichika, T. Imasaka, and N. Ishibashi, Ion-selective optrode using hexadecyl-acridine orange attached on poly(vinyl chloride) membrane, Anal. Chem, 62, 2054-2055 (1990). 

Friedel-Crafts acylation fails with quinoline, isoquinoline, acridine and many derivatives. However, when sufficient activation is present substitution can result. For example, 8-methoxyquinoline (28) in the presence of aluminum chloride and acetyl or benzoyl chloride gives the 5-acetyl and 5-benzoyl derivatives in 25% and 35% yields respectively. 

Many acridines and benzacridines have been synthesized by the Bernthsen reaction (l884LA(224)l) in which a diphenylamine is heated with a carboxylic acid and zinc chloride, with or without aluminum chloride. The reaction has been reviewed (73HC(9)141), and will be outlined here. The yields are not generally high one of the better examples is the synthesis of 2-chloro-9-methylacridine (312) (63BCJ1477). In the synthesis of the... 

The methine bridge in acridines can be derived from dihalomethanes. Originally sodium carbonate was used, with dichloro- or diiodo-methane, to prepare dibenzacridine (624) from 2-naphthylamine (02JCS280). Subsequently, better yields were obtained when dichloromethane, 1,1-dichloroethane or benzal chloride, 1-naphthylamine, and a solvent were heated, the products being dibenz(c,/z jacridines (624) (06JCS1387). 

Ozonolysis of acridine and reduction of the resulting dialdehyde with sodium borohydride gives the diol (179). This is esterified with excess methanesulfonyl chloride and the resulting diester reacts with aqueous ammonia to give the dihydropyrroloquinoline (180). This furnishes the pentacycle (181) with a quantitative yield for the final step (Scheme 55) (75JOC2140). 

Figure 5.13 shows the structures of extrinsic fluors that have been of value in studying biochemical systems. ANS, dansyl chloride, and fluorescein are used for protein studies, whereas ethidium, proflavine, and various acridines are useful for nucleic acid characterization. Ethidium bromide has the unique characteristic of enhanced fluorescence when bound to double-stranded DNA but not to single-stranded DNA. Aminomethyl coumarin (AMC) is of value as a fluorogenic leaving group in measuring peptidase activity. 

Aryliodonium salts have been found to be coinitiators for photooxidizable dye sensitization (105). Smith polymerized aerylamide-bis(acrylamide) mixtures using acridine, xanthene, or cyanine dyes and, for example, diphenyllodonium chloride as an electron acceptor. Reduction of the salt results in the formation of phenyl radicals. 

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