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

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

Procedure: halogenating said compound (B) by diluting the reaction mixture with a protic solvent and introducing a bromine/methanol mixture at -20° to +70° C. to give 1-amino-4-bromo-anthraquinone (C), by diluting the reaction mixture with a protic solvent

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

Procedure: β-aminoanthraquinone; 1,4diaminoanthraquinone; 1,5-diaminoanthraquinone; 1-amino-4-acetylaminoanthraquinone; 1-amino-4-benzoylamino anthraquinone; 1-amino-5-acetylamino-anthraquinone; 1-amino-5-benzoylamino-anthraquinone; 1-amino-4-nitro-anthraquinone; 1-amino-5-nitro-anthraquinone; 1-amino-4-bromo-anthraquinone; 1-amino-4-methylamino-anthraquinone; 1-amino-4-phenylamino-anthraquinone.

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

Procedure: β-aminoanthraquinone; 1,4diaminoanthraquinone; 1,5-diaminoanthraquinone; 1-amino-4-acetylaminoanthraquinone; 1-amino-4-benzoylamino anthraquinone; 1-amino-5-acetylamino-anthraquinone; 1-amino-5-benzoylamino-anthraquinone; 1-amino-4-nitro-anthraquinone; 1-amino-5-nitro-anthraquinone; 1-amino-4-bromo-anthraquinone; 1-amino-4-methylamino-anthraquinone; 1-amino-4-phenylamino-anthraquinone.

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

Procedure: 1-Amino-4-bromoanthraquinone-2-carboxylic acid (38 grams, 0.11 mole) was dissolved in 200 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 (b 0.23 mole) sodium hydrosulfite was added. Heating was continued with stirring for 2 hours, after which the mixture was cooled to room temperature. The resuting solid was collected by filtration and washed with water until the filtrate was neutral. The solid was dried at 80° C. to give 24.9 g (75% yield) of 1-amino-4-bromoanthraquinone. 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 resuting 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: First of all, 17.3 g (0.1 mol) of 3-aminobenzenephosphonic acid was dispersed in a solution of 70 ml of water and 8 g of sodium hydroxide and mixed throughout. To the mixture, 8 g of sodim bicarbonate and 16 g (0.04 mol) of 1-amino-4-bromoanthraquinone were added and 0.6 g of copper chloride was then added and mixed at 70° to 75° C. until the reaction was terminated. The resultant mixture was filtered and the filtrate was made acidic to remove excess 3-aminobenzenephophonic acid. Sodium chloride was added to the filtrate and salted out, filtered and dried. It was then purified with alcohol to obtain a blue anthraquinone compound (20 g). mixed throughout mixed at 70° to 75° C. until the reaction was terminated The resultant mixture was filtered to remove excess 3-aminobenzenephophonic acid Sodium chloride was added to the filtrate filtered dried It was then purified with alcohol

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

Procedure: halogenating said compound (B) by diluting the reaction mixture with a protic solvent and introducing a bromine/methanol mixture at -20° to +70° C. to give 1-amino-4-bromo-anthraquinone (C), by diluting the reaction mixture with a protic solvent

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

Procedure: β-aminoanthraquinone; 1,4diaminoanthraquinone; 1,5-diaminoanthraquinone; 1-amino-4-acetylaminoanthraquinone; 1-amino-4-benzoylamino anthraquinone; 1-amino-5-acetylamino-anthraquinone; 1-amino-5-benzoylamino-anthraquinone; 1-amino-4-nitro-anthraquinone; 1-amino-5-nitro-anthraquinone; 1-amino-4-bromo-anthraquinone; 1-amino-4-methylamino-anthraquinone; 1-amino-4-phenylamino-anthraquinone.