Hydrogen Peroxide → 2-[4-(Ethylisopropylamino)phenylamino)-5-[(2-hydroxyethyl)ethylamino][1,4]benzoquinone

HRID 589305Notes

Reaction equation

HRID 589305 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.[CH2:16]([N:18]1[C:23]2[CH:24]=[C:25]([OH:28])[CH:26]=[CH:27][C:22]=2[O:21][CH2:20][CH2:19]1)[CH3:17].[OH:29]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:26]2[C:25](=[O:28])[CH:24]=[C:23]([N:18]([CH2:19][CH2:20][OH:29])[CH2:16][CH3:17])[C:22](=[O:21])[CH:27]=2)=[CH:8][CH:7]=1)[CH3:14]

Participants

8

Reactant 3

HCID 784Hydrogen PeroxideHCID 16211123N-Ethyl-N-isopropyl-p-phenylenediamine hydrochlorideHCID 896206634-ethyl-3,4-dihydro-2H-1,4-benzoxazin-6-ol hydrobromide

Product 1

HCID 896204922-[4-(Ethylisopropylamino)phenylamino)-5-[(2-hydroxyethyl)ethylamino][1,4]benzoquinone

Reagents, catalysts & solvents 4

HCID 180AcetoneSolventHCID 222AmmoniaSolvent2×HCID 962WaterSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 1.10 g (0.005 mol) of N-(4-aminophenyl)-N-ethyl-N-isopropylamine hydrochloride in 5 ml of water and 3 ml of 20% aqueous ammonia is added a solution of 1.30 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 aqueous hydrogen peroxide solution are added and the mixture is stirred at room temperature for 3 hours 30 minutes. An oil forms. After 12 hours at 6° C., the oil forms a gum. This gum is taken up in ethyl acetate, dried over disodium sulfate and filtered, and the ethyl acetate is evaporated off. The product is purified on a column of silica (eluent: 80/20 ethyl acetate/heptane). The eluent is evaporated off. After 48 hours at 6° C., the product has crystallized, and is left to dry. 0.52 g of 2-[4-(ethylisopropylamino)phenylamino)-5-[(2-hydroxyethyl)ethylamino][1,4]benzoquinone (compound 11) is obtained.

Workup

  1. waitAfter 12 hours at 6° C.
  2. dry with materialdried over disodium sulfate
  3. filtrationfiltered
  4. customthe ethyl acetate is evaporated off
  5. customThe product is purified on a column of silica (eluent: 80/20 ethyl acetate/heptane)
  6. customThe eluent is evaporated off
  7. waitAfter 48 hours at 6° C.
  8. customthe product has crystallized
  9. waitis left
  10. customto dry

Sources & evidence

ORD record
ord-bf831d2af88a4837872b8374a125839b
Source dataset
uspto-grants-2016_01
Patent number
US09233057B2

Reaction notes

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