Methyl Chloride → Acetamide, N-(4-bromo-9,10-dihydro-9,10-dioxo-1-anthracenyl)-N-methyl-

Participants

Reaction Conditions

Reaction Steps

A mixture of 4-bromo-1-acetylaminoanthraquinone (purity 98%, 35.1 g), monochlorobenzene (420 g), tetra-n-butyl ammonium bromide (0.3 g), 96% potassium hydroxide (12.0 g) and potassium iodide (0.5 g) was stirred for 1 hour in an autoclave, while being maintained at 30° C. Then, methyl chloride (10.2 g) was added. The mixture was stirred at 50° C. for 2 hours and 70° C. for 10 hours, successively. After the temperature was lowered to 30° C. and pressure was released, the solution was transferred to a flask by adding water (200 g), and then acetic acid (1.2 g) was added thereto. The aqueous phase had pH of 7. After monochlorobenzene was recovered by heating, the solution was cooled down to 50° C. and filtered. The solid material was washed and dried to obtain 4-bromo-N-acetyl-1-methylaminoanthraquinone (34.7 g, purity 92.9%, yield 90.0%).

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