Hydrogen Peroxide → 2-[4-(Ethylisopropylamino)phenylamino]-5-[(2-hydroxyethyl)methylamino][1,4]benzoquinone
Reaction equation
Cl.[NH2:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]([CH2:13][CH3:14])[CH:10]([CH3:12])[CH3:11])=[CH:5][CH:4]=1.Br.[CH3:16][N:17]1[C:22]2[CH:23]=[C:24]([OH:27])[CH:25]=[CH:26][C:21]=2[O:20][CH2:19][CH2:18]1.[OH:28]O>O.N.CC(C)=O.C(OCC)(=O)C>[CH2:13]([N:9]([CH:10]([CH3:11])[CH3:12])[C:6]1[CH:5]=[CH:4][C:3]([NH:2][C:25]2[C:24](=[O:27])[CH:23]=[C:22]([N:17]([CH2:18][CH2:19][OH:28])[CH3:16])[C:21](=[O:20])[CH:26]=2)=[CH:8][CH:7]=1)[CH3:14]Participants
8
Reactant 3
Product 1
Reagents, catalysts & solvents 4
Procedure
To a solution of 1.07 g (0.005 mol) of N-(4-aminophenyl)-N-ethyl-N-isopropylamine hydrochloride in 5 ml of water and 2 ml of 20% aqueous ammonia is added a solution of 1.22 g (0.005 mol) of 4-methyl-3,4-dihydro-2H-1,4-benzoxazin-6-ol hydrobromide in 2 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 4 hours. An oil forms. After 24 hours at 6° C., the oil forms a gum. This gum is taken up in ethyl acetate. After drying and concentrating this organic phase, 0.86 g of 2-[4-(ethylisopropylamino)phenylamino]-5-[(2-hydroxyethyl)methylamino][1,4]benzoquinone (compound 2) is obtained in the form of a black powder.
Workup
- waitAfter 24 hours at 6° C.
- customAfter drying
- concentrationconcentrating this organic phase
Sources & evidence
- ORD record
- ord-97fcb306fc924d0cb35334d9149657d5
- Source dataset
- uspto-grants-2016_01
- Patent number
- US09233057B2
Reaction notes
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