Disodium 1-amino-4-((3-amino-4-sulfophenyl)amino)-9,10-dihydro-9 → HCID 23670489, compound

HRID 594924Notes

Reaction equation

HRID 594924 reaction equation
[CH:1]1[CH:6]=[C:5]2[C:7]([C:9]3[C:16]([NH:17][C:18]4C=CC(S([O-])(=O)=O)=C(N)C=4)=[CH:15][C:14]([S:29]([O-:32])(=[O:31])=[O:30])=[C:13]([NH2:33])[C:10]=3[C:11](=[O:12])[C:4]2=[CH:3][CH:2]=1)=[O:8].[Na+:34].[Na+].[O-][Mn](=O)(=O)=O.[K+]>CC(O)=O.O>[CH3:18][NH:17][C:16]1[C:9]2[C:7]([C:5]3[C:4]([C:11](=[O:12])[C:10]=2[C:13]([NH2:33])=[C:14]([S:29]([O-:32])(=[O:31])=[O:30])[CH:15]=1)=[CH:3][CH:2]=[CH:1][CH:6]=3)=[O:8].[Na+:34]

Participants

5

Reactant 2

HCID 165525Disodium 1-amino-4-((3-amino-4-sulfophenyl)amino)-9,10-dihydro-9HCID 516875Potassium Permanganate

Product 1

HCID 23670489HCID 23670489, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

To a suspension of AQ-1 (51.5 g, 343 mmol) in AcOH (500 mL) is added a solution of KMnO4 (59.7 g, 36.6 mmol) in H2O (500.0 mL) dropwise at 5° C. The reaction mixture is then stirred at rt for 1 h. The mixture is extracted with EtOAc, washed with aq. NaHCO3, dried (Na2SO4) and concentrated. The resultant residue is purified by recrystallization to yield AQ-2.

Workup

  1. extractionThe mixture is extracted with EtOAc
  2. washwashed with aq. NaHCO3
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated
  5. customThe resultant residue is purified by recrystallization

Sources & evidence

ORD record
ord-97ecb3d0a5b5400fb4d33a5bb4ab79f9
Source dataset
uspto-grants-2016_01
Patent number
US09242989B2

Reaction notes

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