1-amino-2-methylanthracene-9,10-dione

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

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

Procedure: The wet filter cake of 1-nitro-2-methylanthraquinone (0.45 mole) was placed in a 5 l flask. To the flask was added 420 g (1.75 mole) of Na2S.9H2O dissolved in 2.5 l of H2O and the slurry was heated and then stirred at 95°-99° C. for 2 hours. The reaction mixture was filtered and the orangish-red solid 1-amino-2-methylanthraquinone product was washed with hot H2O until the filtrate was clear and dried in vacuo at 70° C. the slurry was heated The reaction mixture was filtered the orangish-red solid 1-amino-2-methylanthraquinone product was washed with hot H2O until the filtrate dried in vacuo at 70° C.

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

Procedure: The wet filter cake of 1-nitro-2-methylanthraquinone (0.45 mole) was placed in a 5 l flask. To the flask was added 420 g (1.75 mole) of Na2S.9H2O dissolved in 2.5 l of H2O and the slurry was heated and then stirred at 95°-99° C. for 2 hours. The reaction mixture was filtered and the orangish-red solid 1-amino-2-methylanthraquinone product was washed with hot H2O until the filtrate was clear and dried in vacuo at 70° C. the slurry was heated The reaction mixture was filtered the orangish-red solid 1-amino-2-methylanthraquinone product was washed with hot H2O until the filtrate dried in vacuo at 70° C.

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

Procedure: 53 parts of 1-nitro-2-methylanthraquinone and 0.6 part of 2,3-dichloro-1,4-naphthoquinone in 300 parts by volume of ethanol and 150 parts by volume of 50% aqueous sodium hydroxide solution are heated to 78°-80° C. At this temperature, 37% aqueous formaldehyde solution is added dropwise to the solution in accordance with the consumption. The consumption of formaldehyde can be checked and the addition controlled by measuring the changes in the redox potential. The time taken for the addition is 11/2 to 2 hours. The 1-amino-2-methylanthraquinone so obtained is then completely precipitated by addition of water, and the precipitate is isolated by filtration, washed with water and dried in vacuo at 80° C. Yield: about 43 g (~90% of theory) of 1-amino-2-methylanthraquinone. The consumption of formaldehyde the addition The time taken for the addition 2 to 2 hours

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

Procedure: 53 parts of 1-nitro-2-methylanthraquinone and 0.6 part of 2,3-dichloro-1,4-naphthoquinone in 300 parts by volume of ethanol and 150 parts by volume of 50% aqueous sodium hydroxide solution are heated to 78°-80° C. At this temperature, 37% aqueous formaldehyde solution is added dropwise to the solution in accordance with the consumption. The consumption of formaldehyde can be checked and the addition controlled by measuring the changes in the redox potential. The time taken for the addition is 11/2 to 2 hours. The 1-amino-2-methylanthraquinone so obtained is then completely precipitated by addition of water, and the precipitate is isolated by filtration, washed with water and dried in vacuo at 80° C. Yield: about 43 g (~90% of theory) of 1-amino-2-methylanthraquinone. The consumption of formaldehyde the addition The time taken for the addition 2 to 2 hours

Conditions: temp:40.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 1-amino-2-methylanthraquinone (300 g) is slurried with 1500 ml of HOAc in a 5-liter flask. The temperature is raised to 40° C. Neat bromine (405 g) is added over a 21/2 hours with stirring at 40°-50° C. The mixture is stirred for 20 additional minutes and filtered. The solids so recovered are washed with HOAc and water and sucked dry with an aspirator and transferred to a reaction flask along with 150 g of NaHSO3 and 1.5 liters of water. The mixture is gradually heated to 90° C. (over two hours) with stirring to give 1-amino-2-methyl-4-bromoanthraquinone (AMBAX) as a solid which is recovered from the reaction mixture by filtration in 90% yield, rinsed with water and dried overnight at 155° C. and 1 mm Hg absolute vacuum. ##STR23## The mixture is stirred for 20 additional minutes filtered The solids so recovered are washed with HOAc and water sucked dry with an aspirator transferred to a reaction flask along with 150 g of NaHSO3 and 1.5 liters of water The mixture is gradually heated to 90° C. (over two hours) with stirring

Conditions: temp:40.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 1-amino-2-methylanthraquinone (300 g) is slurried with 1500 ml of HOAc in a 5-liter flask. The temperature is raised to 40° C. Neat bromine (405 g) is added over a 21/2 hours with stirring at 40°-50° C. The mixture is stirred for 20 additional minutes and filtered. The solids so recovered are washed with HOAc and water and sucked dry with an aspirator and transferred to a reaction flask along with 150 g of NaHSO3 and 1.5 liters of water. The mixture is gradually heated to 90° C. (over two hours) with stirring to give 1-amino-2-methyl-4-bromoanthraquinone (AMBAX) as a solid which is recovered from the reaction mixture by filtration in 90% yield, rinsed with water and dried overnight at 155° C. and 1 mm Hg absolute vacuum. ##STR23## The mixture is stirred for 20 additional minutes filtered The solids so recovered are washed with HOAc and water sucked dry with an aspirator transferred to a reaction flask along with 150 g of NaHSO3 and 1.5 liters of water The mixture is gradually heated to 90° C. (over two hours) with stirring

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

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

Procedure: The wet filter cake of 1-nitro-2-methylanthraquinone (0.45 mole) was placed in a 5 l flask. To the flask was added 420 g (1.75 mole) of Na2S·9H2O dissolved in 2.5 l of H2O and the slurry was heated and then stirred at 95°-99° C for 2 hours. The reaction mixture was filtered and the orangish-red solid 1-amino-2-methylanthraquinone product was washed with hot H2O until the filtrate was clear and dried in vacuo at 70° C. the slurry was heated The reaction mixture was filtered the orangish-red solid 1-amino-2-methylanthraquinone product was washed with hot H2O until the filtrate dried in vacuo at 70° C.

Conditions: temp:40.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 1-amino-2-methylanthraquinone (300 g) is slurried with 1500 ml of HOAc in a 5-liter flask. The temperature is raised to 40° C. Neat bromine (405 g) is added over 21/2 hours with stirring at 40°-50° C. The mixture is stirred for 20 additional minutes and filtered. The solids so recovered are washed with HOAc and water and sucked dry with an aspirator and transferred to a reaction flask along with 150 g of NaHSO3 and 1.5 liters of water. The mixture is gradually heated to 90° C. (over two hours) with stirring to give 1-amino-2-methyl-4-bromoanthraquinone as a solid which is recovered from the reaction mixture by filtration in 90% yield, rinsed with water and dried overnight at 155° C. and 1 mm Hg absolute vacuum. The mixture is stirred for 20 additional minutes filtered The solids so recovered are washed with HOAc and water sucked dry with an aspirator transferred to a reaction flask along with 150 g of NaHSO3 and 1.5 liters of water The mixture is gradually heated to 90° C. (over two hours) with stirring

Conditions: temp:40.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 1-Amino-2-methylanthraquinone (300 g) is slurried with 1500 ml of HOAc in a 5-liter flask. The temperature is raised to 40° C. Neat bromine (405 g) is added over 21/2 hours with stirring at 40°-50° C. The mixture is stirred for 20 additional minutes and filtered. The solids so recovered are washed with HOAc and water and sucked dry with an aspirator and transferred to a reaction flask along with 150 g of NaHSO3 and 1.5 liters of water. The mixture is gradually heated to 90° C. (over two hours) with stirring to give 1-amino-2-methyl-4-bromoanthraquinone (A) (also marketed as AMBAX) as a solid which is recovered from the reaction mixture by filtration in 90% yield, rinsed with water and dried overnight at 155° C. and 1 mm Hg absolute vacuum. The mixture is stirred for 20 additional minutes filtered The solids so recovered are washed with HOAc and water sucked dry with an aspirator transferred to a reaction flask along with 150 g of NaHSO3 and 1.5 liters of water The mixture is gradually heated to 90° C. (over two hours) with stirring

Conditions: temp:40.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 1-Amino-2-methylanthraquinone (300 g) is slurried with 1500 ml of HOAc in a 5-liter flask. The temperature is raised to 40° C. Neat bromine (405 g) is added over 21/2 hours with stirring at 40°-50° C. The mixture is stirred for 20 additional minutes and filtered. The solids to recovered are washed with HOAc and water and sucked dry with an aspirator and transferred to a reaction flask along with 150 g of NaHSO3 and 1.5 liters of water. The mixture is gradually heated to 90° C. (over two hours) with stirring to give 1-amino-2-methyl-4-bromoanthraquinone (A) (also marketed as AMBAX) as a solid which is recovered from the reaction mixture by filtration in 90% yield, rinsed with water and dried overnight at 155° C. and 1 mm Hg absolute vacuum. The mixture is stirred for 20 additional minutes filtered The solids to recovered are washed with HOAc and water sucked dry with an aspirator transferred to a reaction flask along with 150 g of NaHSO3 and 1.5 liters of water The mixture is gradually heated to 90° C. (over two hours) with stirring