Acridine Yellow G

From the same class of light sensitive and heat resistant polymers, poly[4,4 -hexafluoro-isopropylidene)-diphthalic anhydride-a/f-acridine yellow G], HCI is given as another example. The structure of this polymer is shown below ... 

Figure 13.4.2. Variation of weight % loss forpoly[4,4 -hexafluoro-isopropylidene)-diphthalic anhydride-alt-acridine yellow G] HCI in a TGA experiment at a heating rate of 10P C/min.

The TGA curve indicates a complex decomposition process. The Py-GC/MS result for poly[4,4 -hexafluoro-isopropylidene)-diphthalic anhydride-aff-acridine yellow G] HCI is given in Figure 13.4.3. This is a light sensitive polymer (X max. 273 nm) but also with high heat resistance, and the pyrolysis was performed at 850 C in He. Other conditions were kept similar to those for other examples previously described (see Table 4.2.2). The separation was done on a Carbowax column. The peak identification was done using MS spectral library searches only and is given in Table 13.4.4. 

Figure 13.4.3. Pyrogram from Py-GC/MS analysis of poly[4,4 -hexafluoro-isopropylidene)diphthalic anhydride-alt-acridine yellow G] HCI. Pyrolysis done on 0.4 mg material at 85(f C in He, with the separation on a Carbowax type column.

Acridine Yeiiow G (2,7-dimethylacridine-3,6-diamine hydrochloride)/775-49-9/ M 273.8, m 325 (free base). Cl 46025, pKj -3.0, pKl 0.5, pKl 8.9. Note that the hydrochloride is normally called Acridine Yellow G and not the free base. The free base recrystallises from 1 1 benzene/methanol, or from 800 parts of EtOH. It is converted to the sparingly soluble hydrochloride with dilute HCl, filtered off and dried. [Albert 7 Chem Soc 248 1947, Beilstein 22 IIEIV 5499,22/11 V 340.]... 

Acridine dyes are amino derivatives of acridine. Acridine yellow G 40 is prepared by a similar method to pyronine G (see p 266) from 2,4-diaminotoluene via the leuco compound 39 by a Bernthsen synthesis. 

Acridine yellow, in D-00079 Astrafloxine G Chloride, in A-00450 Astrazon blue B Chloride, in A-00452 Benzenecarbothioic acid 2-hydroxy(di-2-... 

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. 

By bonding two phenyl rings via a heteroatom bridge in the 2- and 2 -positions, the yellow acridine dyes (4a), the red to violet xanthene dyes (4b), or similarly colored thioxanthene dyes (4c) in the case of amino-substituted di- or triaiyl-methane dyes are obtained. Because of their rigid molecular skeletons these compounds fluoresce. Hydroxyxanthenes behave similarly (e.g., fluorescein) [2],... 

In order to obtain the base in a state of absolute purity Koenigs dissolves 10 g. in 50 cc. of alcohol and adds a solution of 10 g of tartaric add in 100 cc. of alcohol. The tartrate which separates is washed with alcohol, dissolved in water, and converted into the base with ammonia. The acridine should then form greenish yellow needles which melt at 117-8°. 

Yellow crystals. Acid reaction. Forms a water-sol sodium salt. Can be pptd as a water -insol salt by acridine derivs such as acriflavlne, by sulfa drugs such as homosulfanil-amide, by basic antibiotics such as streptomycin base, by enzymes such as papain and lysozyme, by dyes such as methylene blue, and by metallic salts such as CaCl2. LDW j.p. in mice 0-05 mg/ 10-12 g mouse (Hosoya). 

A group of yellow, weakly-basic alkaloids derived from acridine. A. occur exclusively in the Ru-taceae (in bark, wood, leaves, roots e. g., Euodia xan-thoxyloides) especially in more than 20 species of the subfamilies Rutoideae, Toddalioideae, and Aurantioi-deae. Most of the naturally occurring A. (>100) are methylated at N and cany oxygen functions at posi-... 

The acridine-9-nitrile (15 g, 70 mM) is added to cone, sulphuric acid (120 ml) and heated on a steam bath for 2.5 hours. It is cooled to 0 °C in an iced water bath and sodium nitrite (55 g, 7.5 M) is slowly added so that brown fumes are evolved. The mixture is then carefully heated with a bunsen burner until no more gas is given off. It is then stirred at 100 °C for 2 hours, cooled and slowly poured into iced water to precipitate the yellow product. This is filtered off, washed with water and sucked dry. The product is then dissolved in the minimum of 2M NaOH solution and filtered through a sintered funnel. The deep red solution is treated with cone. HCl until the yellow precipitate has permanently reformed. This is filtered, washed with water and sucked dry. It is further dried at 55 °C under reduced pressure for 24 hours (14.7g, 65mM, 89%), (i.r 1650cm acid C=0). 

Acridine-9-carboxylic acid is refluxed in a large excess of redistilled thionyl chloride under dry conditions until solution is complete (ca. 3 hours). The reagent is evaporated off (any residue of thionyl chloride being removed by co-evaporation with dry benzene) to give a yellow powder that is used without further purification (IR 1780cm" Cl—G=0). 

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