Hydrogen Peroxide → 2-[4-(Ethylisopropylamino)phenylamino)-5-[(2-hydroxyethyl)ethylamino][1,4]benzoquinone

Participants

Reaction Steps

To a solution of 1.10 g (0.005 mol) of N-(4-aminophenyl)-N-ethyl-N-isopropylamine hydrochloride in 5 ml of water and 3 ml of 20% aqueous ammonia is added a solution of 1.30 g (0.005 mol) of 4-ethyl-3,4-dihydro-2H-1,4-benzoxazin-6-ol hydrobromide in 3 ml of water, 1 ml of 20% aqueous ammonia and 15 ml of acetone. 17 ml of aqueous hydrogen peroxide solution are added and the mixture is stirred at room temperature for 3 hours 30 minutes. An oil forms. After 12 hours at 6° C., the oil forms a gum. This gum is taken up in ethyl acetate, dried over disodium sulfate and filtered, and the ethyl acetate is evaporated off. The product is purified on a column of silica (eluent: 80/20 ethyl acetate/heptane). The eluent is evaporated off. After 48 hours at 6° C., the product has crystallized, and is left to dry. 0.52 g of 2-[4-(ethylisopropylamino)phenylamino)-5-[(2-hydroxyethyl)ethylamino][1,4]benzoquinone (compound 11) is obtained.

Provenance & Evidence