Hydrogen Peroxide → 2-(3-Chloro-4-hydroxyphenylamino)-5-[(2-hydroxyethyl)methylamino][1,4]benzoquinone

HRID 589306Notes

Reaction equation

HRID 589306 reaction equation
Cl.[NH2:2][C:3]1[CH:8]=[CH:7][C:6]([OH:9])=[C:5]([Cl:10])[CH:4]=1.Br.[CH3:12][N:13]1[C:18]2[CH:19]=[C:20]([OH:23])[CH:21]=[CH:22][C:17]=2[O:16][CH2:15][CH2:14]1.[OH:24]O>O.N.CC(C)=O>[Cl:10][C:5]1[CH:4]=[C:3]([NH:2][C:21]2[C:20](=[O:23])[CH:19]=[C:18]([N:13]([CH2:14][CH2:15][OH:24])[CH3:12])[C:17](=[O:16])[CH:22]=2)[CH:8]=[CH:7][C:6]=1[OH:9]

Participants

7

Reactant 3

HCID 784Hydrogen PeroxideHCID 198076694-Amino-2-chlorophenol hydrochlorideHCID 896208084-methyl-3,4-dihydro-2H-1,4-benzoxazin-6-ol hydrobromide

Product 1

HCID 896207812-(3-Chloro-4-hydroxyphenylamino)-5-[(2-hydroxyethyl)methylamino][1,4]benzoquinone

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 222AmmoniaSolvent3×HCID 962WaterSolvent2×

Procedure

To a solution of 0.90 g (0.005 mol) of 4-amino-2-chlorophenol hydrochloride in 5 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. The pH is adjusted to 9.5 with 20% aqueous ammonia. 17 ml of 6% aqueous hydrogen peroxide solution are added. After 3 hours, the precipitate is filtered off. 0.99 g of 2-(3-chloro-4-hydroxyphenylamino)-5-[(2-hydroxyethyl)methylamino][1,4]benzoquinone (compound 7) is obtained in the form of a brown powder.

Workup

  1. filtrationthe precipitate is filtered off

Sources & evidence

ORD record
ord-598d497d7ab34b13ac02eaf0b356983c
Source dataset
uspto-grants-2016_01
Patent number
US09233057B2

Reaction notes

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