1-(methylamino)anthracene-9,10-dione

Conditions: temp:30.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 1-aminoanthraquinone (purity 99.6%, 22.4 g), monochlorobenzene (224 g), tetra-n-butyl ammonium bromide (3.4 g), 96% potassium hydroxide (11.7 g) and dimethylsulfuric acid (25 g) was stirred while being maintained at 30° C. for 24 hours. After water (150 g) was added, the solution was stirred for 1 hour, being maintained at 50° C. pH of the aqueous phase was 10 or higher. Then, acetic acid (0.5 g) was added for neutralization (pH of the aqueous phase being 7) and then monochlorobenzene was recovered by heating. After being cooled down to 50° C., the solution was filtered, and a solid was washed and then dried to obtain 1-methylaminoanthraquinone (23.7 g, purity 97.6%, yield 97.6%). the solution was stirred for 1 hour being maintained at 50° C. pH of the aqueous phase was recovered by heating After being cooled down to 50° C. the solution was filtered a solid was washed dried

Conditions: temp:30.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 1-aminoanthraquinone (purity 99.6%, 22.4 g), nitrobenzene (224 g), 96% potassium hydroxide (11.7 g), tetra-n-butyl ammonium bromide (1.7 g) and dimethylsulfuric acid (25 g) was stirred, while being maintained at 30° C. for 24 hours. Then, after water (150 g) was added, the solution was stirred for one hour while being maintained at 50° C. The aqueous phase had pH of 10 or higher. After acetic acid (0.5 g) was added for neutralization until pH of the aqueous phase was 7, nitrobenzene was recovered. The solution was cooled down to 50° C., and filtered. The solid material was washed and dried, to obtain 1-methylaminoanthraquinone (23.7 g, purity: 99.5%, yield 99.5%). the solution was stirred for one hour while being maintained at 50° C was recovered The solution was cooled down to 50° C. filtered The solid material was washed dried