Hydrogen Peroxide → 2-(4-Amino-2,3-dimethylphenylamino)-5-[(2-hydroxyethyl)ethylamino][1,4]benzoquinone
Reaction equation
Cl.Cl.[CH3:3][C:4]1[C:9]([CH3:10])=[C:8]([NH2:11])[CH:7]=[CH:6][C:5]=1[NH2:12].Br.[CH2:14]([N:16]1[C:21]2[CH:22]=[C:23]([OH:26])[CH:24]=[CH:25][C:20]=2[O:19][CH2:18][CH2:17]1)[CH3:15].[OH:27]O>O.N.CC(C)=O>[NH2:11][C:8]1[CH:7]=[CH:6][C:5]([NH:12][C:24]2[C:23](=[O:26])[CH:22]=[C:21]([N:16]([CH2:17][CH2:18][OH:27])[CH2:14][CH3:15])[C:20](=[O:19])[CH:25]=2)=[C:4]([CH3:3])[C:9]=1[CH3:10]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 3
Procedure
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.
Workup
- waitAfter 12 hours at 6° C.
- concentrationthe reaction medium is concentrated
- waitleft for a further 12 hours at 6° C
- filtrationA precipitate forms, which is filtered off
- customIt is purified by chromatography
- washeluting with dichloromethane/methanol
Sources & evidence
- ORD record
- ord-d7f7020f8d69445d81d7d84da71c0b79
- Source dataset
- uspto-grants-2016_01
- Patent number
- US09233057B2
Reaction notes
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