1,4-dimethoxyanthracene-9,10-dione

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

Procedure: 1,4-Diaminobutane (1.65 g, 19 mmol) was added to a solution of 1,4-dimethoxyanthracene-9,10-dione (1.0 g, 3.7 mmol) in CH2Cl2 (700 ml). After seven, hours of irradiation, the solvent was removed and the residue chromatographed on silica gel. Starting material was eluted with CHCl3 and the product with 5% CH3OH in CHCl3. A purple solid (0.61 g, 50%) was obtained which was converted to the benzyloxycarbonyl derivative. After seven, hours of irradiation the solvent was removed the residue chromatographed on silica gel Starting material was eluted with CHCl3

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

Procedure: A solution of 1,3-diaminopropane (2.07 g, 28 mmol) and 1,4 dimethoxyanthraquinone (1.50 g, 5.6 mmol) in freshly distilled CH2Cl2 (1.5 l) was fitted with a reflux condenser, and irradiated with a sunlamp for 6 h. The solvent was distilled and the crude mixture was dried in vacuo overnight. The crude product was triturated with warm petroleum ether to remove excess amine. Chromatography (silica gel CCl4 and CH2Cl2, 1:1) was performed by slowly increasing the polarity of the solvent to CH2Cl2 to remove the unreacted 1,4-dimethoxyanthraquinone. Upon elution with methanol, a purple band slowly developed. A purple oil remained upon removal of the solvent. The oil was extracted with warm CCl4, and crystallized by adding petroleum ether to the combined CCl4 extracts. Crystallization afforded a purple solid, 0.48 g (28%) in three crops. Recrystallization from a mixture of CCl4 and petroleum ether afforded an analytical sample: mp 108°-110° C.; 1H NMR (CDCl3)δ9.95 (broad t, 1H), 8.21-8.25 (m, 2 H), 7.68-7.73 (m, 2 H), 7.37 (d, 1 H), 7.17 (d, 1H), 4.00(s, 3 H), 3.39-3.48 (m, 2 H), 2.94 (t,2 H), 1.86-1.98 (m, 2 H), 1.36 (broad s, 2H). Anal. Calcd. for C18H18N2O3 : C, 69.66; H, 5.85, N, 9.03. Found: C, 69.75; H 5.95; N, 8.95. irradiated with a sunlamp for 6 h The solvent was distilled the crude mixture was dried in vacuo overnight The crude product was triturated with warm petroleum ether to remove excess amine by slowly increasing the polarity of the solvent to CH2Cl2 to remove the unreacted 1,4-dimethoxyanthraquinone Upon elution with methanol A purple oil remained upon removal of the solvent The oil was extracted with warm CCl4 crystallized by adding petroleum ether to the combined CCl4 Crystallization afforded a purple solid, 0.48 g (28%) in three crops Recrystallization from a mixture of CCl4 and petroleum ether afforded an analytical sample

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

Procedure: 1,4-Diaminobutane (1.65 g, 19 mmol) was added to a solution of 1,4-dimethoxyanthracene-9,10-dione (1.0 g, 3.7 mmol) in CH2Cl2 (700 ml). After seven, hours of irradiation, the solvent was removed and the residue chromatographed on silica gel. Starting material was eluted with CHCl3 and the product with 5% CH3OH in CHCl3. A purple solid (0.61 g, 50%) was obtained which was converted to the benzyloxycarbonyl derivative. After seven, hours of irradiation the solvent was removed the residue chromatographed on silica gel Starting material was eluted with CHCl3

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

Procedure: 1,4-Diaminobutane (1.65 g, 19 mmol) was added to a solution of 1,4-dimethoxyanthracene-9,10-dione (1.0 g, 3.7 mmol) in CH2Cl2 (700 ml). After seven, hours of irradiation, the solvent was removed and the residue chromatographed on silica gel. Starting material was eluted with CHCl3 and the product with 5% CH3OH in CHCl3. A purple solid (0.61 g, 50%) was obtained which was converted to the benzyloxycarbonyl derivative. After seven, hours of irradiation the solvent was removed the residue chromatographed on silica gel Starting material was eluted with CHCl3

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

Procedure: A solution of 1,3-diaminopropane (2.07 g, 28 mmol) and 1,4 dimethoxyanthraquinone (1.50 g, 5.6 mmol) in freshly distilled CH2Cl2 (1.5 l) was fitted with a reflux condenser, and irradiated with a sunlamp for 6 h. The solvent was distilled and the crude mixture was dried in vacuo overnight. The crude product was triturated with warm petroleum ether to remove excess amine. Chromatography (silica gel CCl4 and CH2Cl2, 1:1) was performed by slowly increasing the polarity of the solvent to CH2Cl2 to remove the unreacted 1,4-dimethoxyanthraquinone. Upon elution with methanol, a purple band slowly developed. A purple oil remained upon removal of the solvent. The oil was extracted with warm CCl4, and crystallized by adding petroleum ether to the combined CCl4 extracts. Crystallization afforded a purple solid, 0.48 g (28%) in three crops. Recrystallization from a mixture of CCl4 and petroleum ether afforded an analytical sample: mp 108°-110° C.; 1H NMR (CDCl3)δ9.95 (broad t, 1H), 8.21-8.25 (m, 2 H), 7.68-7.73 (m, 2 H), 7.37 (d, 1 H), 7.17 (d, 1H), 4.00(s, 3 H), 3.39-3.48 (m, 2 H), 2.94 (t,2 H), 1.86-1.98 (m, 2 H), 1.36 (broad s, 2H). Anal. Calcd. for C18H18N2O3 : C, 69.66; H, 5.85, N, 9.03. Found: C, 69.75; H 5.95; N, 8.95. irradiated with a sunlamp for 6 h The solvent was distilled the crude mixture was dried in vacuo overnight The crude product was triturated with warm petroleum ether to remove excess amine by slowly increasing the polarity of the solvent to CH2Cl2 to remove the unreacted 1,4-dimethoxyanthraquinone Upon elution with methanol A purple oil remained upon removal of the solvent The oil was extracted with warm CCl4 crystallized by adding petroleum ether to the combined CCl4 Crystallization afforded a purple solid, 0.48 g (28%) in three crops Recrystallization from a mixture of CCl4 and petroleum ether afforded an analytical sample

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

Procedure: A solution of 1,3-diaminopropane (2.07 g, 28 mmol) and 1,4 dimethoxyanthraquinone (1.50 g, 5.6 mmol) in freshly distilled CH2Cl2 (1.5 l) was fitted with a reflux condenser, and irradiated with a sunlamp for 6 h. The solvent was distilled and the crude mixture was dried in vacuo overnight. The crude product was triturated with warm petroleum ether to remove excess amine. Chromatography (silica gel CCl4 and CH2Cl2, 1:1) was performed by slowly increasing the polarity of the solvent to CH2Cl2 to remove the unreacted 1,4-dimethoxyanthraquinone. Upon elution with methanol, a purple band slowly developed. A purple oil remained upon removal of the solvent. The oil was extracted with warm CCl4, and crystallized by adding petroleum ether to the combined CCl4 extracts. Crystallization afforded a purple solid, 0.48 g (28%) in three crops. Recrystallization from a mixture of CCl4 and petroleum ether afforded an analytical sample: mp 108°-110° C.; 1H NMR (CDCl3)δ9.95 (broad t, 1H), 8.21-8.25 (m, 2 H), 7.68-7.73 (m, 2 H), 7.37 (d, 1 H), 7.17 (d, 1H), 4.00(s, 3 H), 3.39-3.48 (m, 2 H), 2.94 (t,2 H), 1.86-1.98 (m, 2 H), 1.36 (broad s, 2H). Anal. Calcd. for C18H18N2O3 : C, 69.66; H, 5.85, N, 9.03. Found: C, 69.75; H 5.95; N, 8.95. irradiated with a sunlamp for 6 h The solvent was distilled the crude mixture was dried in vacuo overnight The crude product was triturated with warm petroleum ether to remove excess amine by slowly increasing the polarity of the solvent to CH2Cl2 to remove the unreacted 1,4-dimethoxyanthraquinone Upon elution with methanol A purple oil remained upon removal of the solvent The oil was extracted with warm CCl4 crystallized by adding petroleum ether to the combined CCl4 Crystallization afforded a purple solid, 0.48 g (28%) in three crops Recrystallization from a mixture of CCl4 and petroleum ether afforded an analytical sample

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

Procedure: In accordance with the above procedure, but where in place of 1,4-dimethoxyanthraquinone there is utilized 1,4,5,8-tetramethoxyanthraquinone, there is obtained the corresponding 1,4-dimethoxy-5,8,9,10-anthradiquinone as a purple solid, m.p. 277-278; NMR: δ 3.96 (s, 6H), 6.89 (s, 2H), 7.37 (s, 2H); IR: 5.93, 6.10, 6.41 microns.

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

Procedure: In accordance with the above procedure, but where in place of 1,4-dimethoxyanthraquinone there is utilized 1,4,5,8-tetramethoxyanthraquinone, there is obtained the corresponding 1,4-dimethoxy-5,8,9,10-anthradiquinone as a purple solid, m.p. 277-278; NMR: δ 3.96 (s, 6H), 6.89 (s, 2H), 7.37 (s, 2H); IR: 5.93, 6.10, 6.41 microns.

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

Procedure: 1,4-Dimethoxyanthraquinone (II) (0.596 g, 2 mmole) is dissolved in hot aceton (60 ml) and argentic oxide (1g, 8mmole) was added to this warm solution. Brief sonication forms a uniform dispersal of oxident. The mixture is heated up to boiling on steam bath again and the mixture stirred vigorously with magnetic stirrer. The oxidation is then initiated by the addition of 6N aqueous nitric acid (2 ml). After addition, the mixture is stirred while cooling for an extra 20 minutes and filtered. The residue is washed thoroughly with water and dried under reduced pressure to give quinizarinquinone (III) as a brown solid. Brief sonication forms a uniform dispersal of oxident The mixture is heated up to boiling on steam bath After addition the mixture is stirred while cooling for an extra 20 minutes filtered The residue is washed thoroughly with water dried under reduced pressure

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

Procedure: 1,4-Dimethoxyanthraquinone (II) (0.596 g, 2 mmole) is dissolved in hot aceton (60 ml) and argentic oxide (1g, 8mmole) was added to this warm solution. Brief sonication forms a uniform dispersal of oxident. The mixture is heated up to boiling on steam bath again and the mixture stirred vigorously with magnetic stirrer. The oxidation is then initiated by the addition of 6N aqueous nitric acid (2 ml). After addition, the mixture is stirred while cooling for an extra 20 minutes and filtered. The residue is washed thoroughly with water and dried under reduced pressure to give quinizarinquinone (III) as a brown solid. Brief sonication forms a uniform dispersal of oxident The mixture is heated up to boiling on steam bath After addition the mixture is stirred while cooling for an extra 20 minutes filtered The residue is washed thoroughly with water dried under reduced pressure

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

Procedure: 2-(2' ,5'-Dimethoxybenzoyl)-benzoic acid (I) (3 g, 0.01 mole) is added in portions to stirred concentrated sulfuric acid (20 ml). After addition the mixture is heated on steam bath with constant stirring for 20 minutes, cooled to room temperature and poured onto crushed ice (400 g) and extracted with chloroform (3 × 100 ml). The organic extract is washed with 2% aqueous sodium hydroxide solution (10 × 100 ml) and water (100 ml), then dried over anhydrous sodium sulfate and the solvent stripped off under reduced pressure to yield 1,4-dimethoxyanthraquinone (II), as a brownish yellow solid. After addition the mixture is heated on steam bath poured extracted with chloroform (3 × 100 ml) The organic extract is washed with 2% aqueous sodium hydroxide solution (10 × 100 ml) and water (100 ml) dried over anhydrous sodium sulfate

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

Procedure: 1,4-Diaminobutane (1.65 g, 19 mmol) was added to a solution of 1,4-dimethoxyanthracene-9,10-dione (1.0 g, 3.7 mmol) in CH2Cl2 (700 ml). After seven, hours of irradiation, the solvent was removed and the residue chromatographed on silica gel. Starting material was eluted with CHCl3 and the product with 5% CH3OH in CHCl3. A purple solid (0.61 g, 50%) was obtained which was converted to the benzyloxycarbonyl derivative. After seven, hours of irradiation the solvent was removed the residue chromatographed on silica gel Starting material was eluted with CHCl3