10H-anthracen-9-one

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:70.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 2-Chloroethyl-p-toluenesulphonate (6.0 g) was added to a mixture of anthrone (5 g) and potassium carbonate (5 g) in dimethylformamide (130 ml). After stirring for 24 hours at 70° C., the reaction mixture was added to ether. The resultant solution was washed with dilute aqueous potassium hydroxide, dried with magnesium sulphate, and evaporated to yield a crude product which was chromatographed on silica gel, eluting with 4:1 hexane:ethyl acetate, to give 2-(9-anthryloxy)ethyl chloride. The resultant solution was washed with dilute aqueous potassium hydroxide dried with magnesium sulphate evaporated to yield a crude product which was chromatographed on silica gel eluting with 4:1 hexane

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The sulfates of Bu-2659 components are freely soluble in water, slightly soluble in methanol and ethanol but practically insoluble in n-butanol, acetone and other organic solvents. They give positive reactions with ninhydrin and anthrone reagents, but are negative in the Tollens, Fehling and Sakaguchi reactions. The thin layer chromatograms (TLC) of the Bu-2659 components are shown in Table 4 compared with those of neomycin, paromomycin and ribostamycin.

Conditions: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 10,10-Bis[(2-fluoro-4-pyridinyl)methyl]-9(10H)-anthracenone (I) Two solutions are prepared. For one, 1.0 M lithium t-butoxide in THF (1.00 L, 1.00 mol) was added to a solution of anthrone (70.0 g, 0.36 mol) in THF (0.70 L) at 15-30° C. to form lithio anthrone. The second solution was prepared by mixing sodium iodide (45.0 g, 0.30 mol) VI-i (150.0 g, 0.73 mol) and THF (1.60 L) at 40° C. for 3 h to form a mixture of VI-i/VII-i. The lithio anthrone solution was added dropwise over 100 min at 40-50° C. to the iodide/mesylate solution. The reaction was aged for 1 h (the HPLC peak area of VII-i was <1%). The solution was washed with saturated aqueous brine (2×0.90 L). Volatiles were removed in vacuo and the residue was diluted with toluene (1.3 L). The solution was heated to 100° C., cooled to 90° C. and stirred with basic alumina (120 g) for 30 min. The solution was filtered through a Celite pad, concentrated by atmospheric distillation to 500 mL and cooled to 25° C. to crystallize I. Further crystallization was induced by the dropwise addition of n-heptane (0.60 L) followed by cooling to 0° C. for 2 h. The crystals were collected by filtration, washed with n-heptane (0.2 L) and dried at 60° C. in vacuo to yield 121 g of I (75% yield from anthrone, 92 HPLC wt % purity versus a reference standard). The second solution was prepared to form a mixture of VI-i/VII-i The solution was washed with saturated aqueous brine (2×0.90 L) Volatiles were removed in vacuo the residue was diluted with toluene (1.3 L) cooled to 90° C. The solution was filtered through a Celite pad concentrated by atmospheric distillation to 500 mL cooled to 25° C. to crystallize I Further crystallization was induced by the dropwise addition of n-heptane (0.60 L) by cooling to 0° C. for 2 h The crystals were collected by filtration washed with n-heptane (0.2 L) dried at 60° C. in vacuo

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The individual BBM-1675 components show solubility and color reactions similar to each other. For example, they are soluble in chloroform, ethyl acetate, acetone, ethanol and methanol, slightly soluble in benzene and water, and insoluble in n-hexane and carbon tetrachloride. They give positive reactions with ferric chloride, Ehrlich and Tollen's reagents but negative responses in Sakaguchi, ninhydrin and anthrone tests.

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The individual BBM-1675 components show solubility and color reactions similar to each other. For example, they are soluble in chloroform, ethyl acetate, acetone, ethanol and methanol, slightly soluble in benzene and water, and insoluble in n-hexane and carbon tetrachloride. They give positive reactions with ferric chloride, Ehrlich and Tollen's reagents but negative responses in Sakaguchi, ninhydrin and anthrone tests.

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: After hydrochloric acid was added to an acetic acid solution of anthrone, it was refluxed upon addition of zinc. Thereafter it was refined in accordance with an ordinary method to obtain 9,9′-bianthryl. After it was added little by little to a melt of aluminum chloride and sodium chloride, the reaction mixture was poured into diluted hydrochloric acid and a solids constituent was collected. The solids constituent thus obtained was refined in accordance with an ordinary method to obtain target dibenzo[a,o]perylene.

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: After hydrochloric acid was added to an acetic acid solution of anthrone, it was refluxed upon addition of zinc. Thereafter it was refined in accordance with an ordinary method to obtain 9,9′-bianthryl. After it was added little by little to a melt of aluminum chloride and sodium chloride, the reaction mixture was poured into diluted hydrochloric acid and a solids constituent was collected. The solids constituent thus obtained was refined in accordance with an ordinary method to obtain target dibenzo[a,o]perylene.

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: According to a method reported by Sieglitz and Marx, Berichte 56, 1619(1923) and by F. H. C. Stuart, Australian J. Chem., 478(1960), 8.2 g of 9-benzyl-anthracene was synthesized from 18.9 g of anthrone and 50 g of benzyl bromide. A solution of 4.8 g of 9-benzyl bromide in 40 ml of acetic acid was chloromethylated with 3.2 g of paraformaldehyde and hydrochloride gas to give 3.4 g of 9-benzyl-10-chloromethylanthracene (mp: 146° to 147° C.) after recrystallization from benzene.

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: According to a method reported by Sieglitz and Marx, Berichte 56, 1619(1923) and by F. H. C. Stuart, Australian J. Chem., 478(1960), 8.2 g of 9-benzyl-anthracene was synthesized from 18.9 g of anthrone and 50 g of benzyl bromide. A solution of 4.8 g of 9-benzyl bromide in 40 ml of acetic acid was chloromethylated with 3.2 g of paraformaldehyde and hydrochloride gas to give 3.4 g of 9-benzyl-10-chloromethylanthracene (mp: 146° to 147° C.) after recrystallization from benzene.

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The individual BBM-1675 components show solubility and color reactions similar to each other. For example, they are soluble in chloroform, ethyl acetate, acetone, ethanol and methanol, slightly soluble in benzene and water, and insoluble in n-hexane and carbon tetrachloride. They give positive reactions with ferric chloride, Ehrlich and Tollen's, reagents but negative responses in Sakaguchi, ninhydrin and anthrone tests.

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of anthrone (5.0 g, 25.7 mmole) in 34 mL anhydrous DMF under an inert atmosphere was added potassium carbonate (7.47 g, 54.1 mmole). To the resulting reaction mixture was added 2-bromoethanol (2.0 mL, 28.3 mmole). The resulting reaction mixture was stirred for 1 hr at room temperature, then 3 hrs at 80° C. The reaction was then cooled to room temperature and quenched with saturated NaHCO3. Ethyl acetate was added and the organic layer was collected and dried over magnesium sulfate. The solvent was concentrated under reduced pressure and the residue was purified via flash chromatography. To the resulting reaction mixture The resulting reaction mixture 3 hrs at 80° C The reaction was then cooled to room temperature quenched with saturated NaHCO3 Ethyl acetate was added the organic layer was collected dried over magnesium sulfate The solvent was concentrated under reduced pressure the residue was purified via flash chromatography