Ammonia → 2-Amino-5-(3'-chloro-4'-hydroxyanilino)-1,4-benzoquinone

HRID 2083127Notes

Reaction equation

HRID 2083127 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([OH:9])[CH:5]=[CH:6][C:7]=1[OH:8].N.OO.Cl.[Cl:14][C:15]1[CH:20]=[C:19]([NH2:21])[CH:18]=[CH:17][C:16]=1[OH:22]>O>[NH2:1][C:2]1[C:7](=[O:8])[CH:6]=[C:5]([NH:21][C:19]2[CH:18]=[CH:17][C:16]([OH:22])=[C:15]([Cl:14])[CH:20]=2)[C:4](=[O:9])[CH:3]=1

Participants

6

Reactant 4

HCID 222AmmoniaHCID 784Hydrogen PeroxideHCID 3017497AminohydroquinoneHCID 198076694-Amino-2-chlorophenol hydrochloride

Product 1

HCID 234675362-Amino-5-(3'-chloro-4'-hydroxyanilino)-1,4-benzoquinone

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

0.02 mole (2.78 g) of 3-amino-4-hydroxy phenol is dissolved in 200 cc of water to which have been added 20 cc of ammonia (22° Be). To this solution there are initially added 100 cc of H2O2 (20 volumes) and the immediately thereafter, with good agitation, 0.02 mole (3.60 g) of 2-chloro-4-amino phenol hydrochloride in 200 cc of water. The reaction mixture is left to stand for 5 hours at ambient temperature at which time it is filtered to recover the 2-amino-5-(3'-chloro-4'-hydroxyanilino)-1,4-benzoquinone which is then washed with water, recrystallized in a mixture of dimethylformamide and water and dried for 5 hours under a vacuum with a boiling water bath. The product is chromatographically pure.

Workup

  1. waitThe reaction mixture is left
  2. filtrationis filtered
  3. customto recover the 2-amino-5-(3'-chloro-4'-hydroxyanilino)-1,4-benzoquinone which
  4. washis then washed with water
  5. customrecrystallized in a mixture of dimethylformamide and water
  6. customdried for 5 hours under a vacuum with a boiling water bath

Sources & evidence

ORD record
ord-215b82e8ba3643439b087dd77ea66751
Source dataset
uspto-grants-1978_04
Patent number
US04084052

Reaction notes

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