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

HRID 589307Notes

Reaction equation

HRID 589307 reaction equation
Cl.[NH2:2][C:3]1[CH:8]=[CH:7][C:6]([OH:9])=[CH:5][C:4]=1[Cl:10].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:4]1[CH:5]=[C:6]([OH:9])[CH:7]=[CH:8][C:3]=1[NH:2][C:21]1[C:20](=[O:23])[CH:19]=[C:18]([N:13]([CH2:14][CH2:15][OH:24])[CH3:12])[C:17](=[O:16])[CH:22]=1

Participants

7

Reactant 3

HCID 784Hydrogen PeroxideHCID 125981904-Amino-3-chlorophenol hydrochlorideHCID 896208084-methyl-3,4-dihydro-2H-1,4-benzoxazin-6-ol hydrobromide

Product 1

HCID 896210782-(2-Chloro-4-hydroxyphenylamino)-5-[(2-hydroxyethyl)methylamino][1,4]benzoquinone

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 222AmmoniaSolvent2×HCID 962WaterSolvent2×

Procedure

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.

Workup

  1. waitAfter 12 hours at 6° C.
  2. customthe precipitate formed
  3. filtrationis filtered off
  4. customdried
  5. customThe product is purified on a column of silica (eluent

Sources & evidence

ORD record
ord-fcaebd8d41aa4094aae166a99ec8e50c
Source dataset
uspto-grants-2016_01
Patent number
US09233057B2

Reaction notes

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