1-amino-4-hydroxyanthracene-9,10-dione

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

Procedure: The progress of the bromination may be followed by thin layer chromatography or high pressure liquid chromatography so as to insure that the byproducts, 1-amino-2-bromoanthraquinone and 1-amino-4-bromoanthraquinone, represent less than 1% of the product mixture. This is essential, since hydroxylation of these two products results in 1-amino-2-hydroxyanthraquinone and 1-amino-4-hydroxyanthraquinone respectively. Both products are isolated along with the desired 1-amino-2-bromo-4-hydroxyanthraquinone and therefore give rise to a product with unsatisfactory quality.

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

Procedure: 70 ml of water, 26.5 g of 1,4-dihydroxyanthraquinone, 1.2 g of hydroxyacetone, 80 g of 25% strength by weight aqueous ammonia solution and 20 g of 50% strength by weight sodium hydroxide solution were introduced into a pressure-resistant apparatus. The apparatus was then sealed pressure-tight and its contents were heated to 100° C., giving rise to an autogenous pressure of 2.7 bar. The reaction mixture was held under these conditions for 3 h, then cooled down and depressurized. The precipitate found was filtered off with suction, washed salt-free with water and dried to leave 15.8 g of 1-amino-4-hydroxyanthraquinone (purity according to GC: 71.1%). giving rise to an autogenous pressure of 2.7 bar cooled down The precipitate found was filtered off with suction washed salt-free with water dried

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

Procedure: 79.5 g of 1,4-dihydroxyanthraquinone, 210 ml of water, 5.6 g of sodium dithionite, 60 g of 50% strength by weight sodium hydroxide solution and 240 g of 25% strength by weight ammonia solution were introduced into a pressure-resistant apparatus. The apparatus was then sealed pressure-tight and its contents were heated to 100° C., giving rise to an autogenous pressure of 2.5 bar. The reaction mixture was held under these conditions for 3 h, then cooled down and depressurized. The precipitate found was filtered off with suction, washed salt-free with water and dried to leave 74.9 g of 1-amino-4-hydroxyanthraquinone (purity according to GC: 90.7%). giving rise to an autogenous pressure of 2.5 bar cooled down The precipitate found was filtered off with suction washed salt-free with water dried

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

Procedure: CH-A-640 873 describes the reaction of 1,4-dihydroxyanthraquinone with ammonia in aqueous phase to form 1-amino-4-hydroxyanthraquinone.

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

Procedure: The progress of the bromination may be followed by thin layer chromatography or high pressure liquid chromatography so as to insure that the byproducts, 1-amino-2-bromoanthraquinone and 1-amino-4-bromoanthraquinone, represent less than 1% of the product mixture. This is essential, since hydroxylation of these two products results in 1-amino-2-hydroxyanthraquinone and 1-amino-4-hydroxyanthraquinone respectively. Both products are isolated along with the desired 1-amino-2-bromo-4-hydroxyanthraquinone and therefore give rise to a product with unsatisfactory quality.

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

Procedure: 70 ml of water, 26.5 g of 1,4-dihydroxyanthraquinone, 1.2 g of hydroxyacetone, 80 g of 25% strength by weight aqueous ammonia solution and 20 g of 50% strength by weight sodium hydroxide solution were introduced into a pressure-resistant apparatus. The apparatus was then sealed pressure-tight and its contents were heated to 100° C., giving rise to an autogenous pressure of 2.7 bar. The reaction mixture was held under these conditions for 3 h, then cooled down and depressurized. The precipitate found was filtered off with suction, washed salt-free with water and dried to leave 15.8 g of 1-amino-4-hydroxyanthraquinone (purity according to GC: 71.1%). giving rise to an autogenous pressure of 2.7 bar cooled down The precipitate found was filtered off with suction washed salt-free with water dried

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

Procedure: 79.5 g of 1,4-dihydroxyanthraquinone, 210 ml of water, 5.6 g of sodium dithionite, 60 g of 50% strength by weight sodium hydroxide solution and 240 g of 25% strength by weight ammonia solution were introduced into a pressure-resistant apparatus. The apparatus was then sealed pressure-tight and its contents were heated to 100° C., giving rise to an autogenous pressure of 2.5 bar. The reaction mixture was held under these conditions for 3 h, then cooled down and depressurized. The precipitate found was filtered off with suction, washed salt-free with water and dried to leave 74.9 g of 1-amino-4-hydroxyanthraquinone (purity according to GC: 90.7%). giving rise to an autogenous pressure of 2.5 bar cooled down The precipitate found was filtered off with suction washed salt-free with water dried

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

Procedure: CH-A-640 873 describes the reaction of 1,4-dihydroxyanthraquinone with ammonia in aqueous phase to form 1-amino-4-hydroxyanthraquinone.

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

Procedure: 1-Amino-4-hydroxyanthraquinone-2-carboxylic acid (31.1 grams, 0.11 mole) was dissolved in 2000 ml. of water and 50 ml. of 10 M sodium hydroxide solution. The mixture was heated on a steam bath to 90°-100° C., and 40 g (0.23 mole) sodium hydro ulfite was added. Heating was continued with stirring for 2 hours, after which the mixture was cooled to room temperature. The resulting solid was collected by filtration and washed with water until the filtrate was neutral. The solid was dried at 80° C. to give 26.2 g (75% yield) of 1-amino-4-hydroxyanthraquinone. The Thin Layer Chromatogram of the crude product showed the presence of a small amount of impurity. The mixture was heated on a steam bath to 90°-100° C. Heating The resulting solid was collected by filtration washed with water until the filtrate The solid was dried at 80° C.

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

Procedure: 1-Amino-4-hydroxyanthraquinone-2-carboxylic acid (31.1 grams, 0.11 mole) was dissolved in 2000 ml. of water and 50 ml. of 10 M sodium hydroxide solution. The mixture was heated on a steam bath to 90°-100° C., and 40 g (0.23 mole) sodium hydro ulfite was added. Heating was continued with stirring for 2 hours, after which the mixture was cooled to room temperature. The resulting solid was collected by filtration and washed with water until the filtrate was neutral. The solid was dried at 80° C. to give 26.2 g (75% yield) of 1-amino-4-hydroxyanthraquinone. The Thin Layer Chromatogram of the crude product showed the presence of a small amount of impurity. The mixture was heated on a steam bath to 90°-100° C. Heating The resulting solid was collected by filtration washed with water until the filtrate The solid was dried at 80° C.

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

Procedure: 22 Parts of α-methacrylic acid are gradually added to a mixture of 23.9 parts of 1-amino-4-hydroxyanthraquinone, 6.2 parts of boric acid and 150 parts of 90% sulphuric acid at 35°-40° C, and the mixture is then stirred for 16 hours at 85°-90° C. The reaction mixture is processed as previously described to give 31 parts (94%) of 1-(β-carboxypropylamino)-4-hydroxyanthraquinone.

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

Procedure: A solution prepared by adding 0.005 part of methoquinone to 24 parts of 1-amino-4-hydroxy-anthraquinone and dissolving the obtained mixture in 900 parts of dried chloroform was cooled with ice in a nitrogen atmosphere. Then, 18 parts of isopropenyl isocyanate was dropped into the resulting solution. After the completion of the dropping, the obtained mixture was stirred under cooling with ice for 3 hours to complete a reaction. Then, the obtained reaction mixture was freed from the chloroform by distillation and recrystallized from ethanol to give a yellow polymerizable anthraquinone dye E. The anthraquinone dye E is represented by the below chemical formula (VI). ##STR6## A solution prepared was cooled with ice in a nitrogen atmosphere under cooling with ice for 3 hours a reaction Then, the obtained reaction mixture was freed from the chloroform by distillation recrystallized from ethanol