Hydrogen Peroxide → 2-(4-Amino-2,3-dimethylphenylamino)-5-[(2-hydroxyethyl)ethylamino][1,4]benzoquinone

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Reaction Steps

To a solution of 1.05 g (0.005 mol) of 2,3-dimethylbenzene-1,4-diamine dihydrochloride in 5 ml of water and 3 ml of 20% aqueous ammonia is added a solution of 1.31 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 6% aqueous hydrogen peroxide solution are added and the mixture is stirred at room temperature for 6 hours 30 minutes. After 12 hours at 6° C., the reaction medium is concentrated and left for a further 12 hours at 6° C. A precipitate forms, which is filtered off. It is purified by chromatography, eluting with dichloromethane/methanol. 0.01 g of 2-(4-amino-2,3-dimethylphenylamino)-5-[(2-hydroxyethyl)ethylamino][1,4]benzoquinone (compound 10) is obtained in the form of a brown powder.

Provenance & Evidence