Réaction #1509600

Équation de réaction

acetic anhydride

4-bromo-1-cyclohexylaminoanthraquinone

sulfuric acid

→

1-(acetylcyclohexylamino)-4-bromoanthraquinone

Rendement 70.1%

Solvants

1,2-dichlorobenzene

methanol

Conditions de réaction

Traitement

1. 1
   AutreAfter the completion of the reaction
2. 2
   Filtrationfiltered

Mode opératoire

102 Grams of acetic anhydride were loaded into a solution of 76.9 g of 4-bromo-1-cyclohexylaminoanthraquinone in 20 g of 1,2-dichlorobenzene and then 1 g of concentrated sulfuric acid was charged into the mixture, followed by stirring at 110° C. for 6 hours. After the completion of the reaction, the reaction product was diluted with 1,000 g of methanol and filtered. Thus, 59.8 g of 1-(acetylcyclohexylamino)-4-bromoanthraquinone were obtained (70.1% yield). Further, a solution of 12 g of caustic soda in 150 g of water was dropped to a solution of 1-(acetylcyclohexylamino)-4-bromoanthraquinone in 150 g of isobutanol and then the mixture was stirred at 90° C. for 6 hours. After the completion of the reaction, the reaction product was cooled and then the resultant solid was separated by filtration. Thus, 28.7 g of 4-bromo-1,9-N-cyclohexylanthrapyridone were obtained (70.4% yield). Next, 19.3 g of 4-methylanilinehexylamine, 8.6 g of sodium carbonate, and 6.8 g of copper powder were loaded into a solution of 20.4 g of 4-bromo-1,9-N-cyclohexylanthrapyridone in 40 g of 1,3-dimethyl-2-imidazolidine, and then the mixture was subjected to a reaction at 190° C. for 4 hours. After the completion of the reaction, the reaction product was cooled, diluted with ethyl acetate, and filtered. The filtrate was purified by column chromatography (toluene/THF). Thus, 17.6 g of a compound (16) were obtained (85.0% yield). FIG. 1 illustrates the 1H-NMR spectrum of the compound (16) in CDCl3 at room temperature and 400 MHz.

Source