Hydrogen Peroxide → 2-(2-Chloro-4-hydroxyphenylamino)-5-[(2-hydroxyethyl)methylamino][1,4]benzoquinone

Participants

Reaction Steps

To a solution of 0.90 g (0.005 mol) of 4-amino-3-chlorophenol hydrochloride in 8 ml of water and 2 ml of 20% aqueous ammonia is added a solution of 1.23 g (0.005 mol) of 4-methyl-3,4-dihydro-2H-1,4-benzoxazin-6-ol hydrobromide in 3 ml of water, 1 ml of 20% aqueous ammonia and 10 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 precipitate formed is filtered off and dried. The product is purified on a column of silica (eluent: 100% dichloromethane and then dichloromethane/methanol up to 10% methanol). 0.01 g of 2-(2-chloro-4-hydroxyphenylamino)-5-[(2-hydroxyethyl)methylamino][1,4]benzoquinone (compound 4) is obtained.

Provenance & Evidence