7-amino-6-bromo-4,4-dimethyl-8-nitroisoquinoline-1,3(2H,4H)-dione → 7,8-Diamino-6-bromo-4,4-dimethylisoquinoline-1,3(2H,4H)-dione

HRID 2253305Notes

Reaction equation

HRID 2253305 reaction equation
[NH2:1][C:2]1[C:11]([N+:12]([O-])=O)=[C:10]2[C:5]([C:6]([CH3:18])([CH3:17])[C:7](=[O:16])[NH:8][C:9]2=[O:15])=[CH:4][C:3]=1[Br:19]>CC(O)=O.[Fe]>[NH2:1][C:2]1[C:11]([NH2:12])=[C:10]2[C:5]([C:6]([CH3:17])([CH3:18])[C:7](=[O:16])[NH:8][C:9]2=[O:15])=[CH:4][C:3]=1[Br:19]

Participants

4

Reactant 1

HCID 596454677-amino-6-bromo-4,4-dimethyl-8-nitroisoquinoline-1,3(2H,4H)-dione

Product 1

HCID 596454907,8-Diamino-6-bromo-4,4-dimethylisoquinoline-1,3(2H,4H)-dioneYield 105.7%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 176Acetic AcidSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 7-amino-6-bromo-4,4-dimethyl-8-nitroisoquinoline-1,3(2H,4H)-dione (2 g, 6.09 mmol) and iron powder (325 mesh, 2.38 g, 42.67 mmol) in AcOH (40 mL) was heated to 70° C. for 8 h. The excess iron was removed using a magnetic bar and the reaction mixture was concentrated under reduced pressure. The residue was diluted with EtOAc, and successively washed with water, aqueous saturated NaHCO3, and brine, dried (MgSO4), filtered and concentrated under reduced pressure to give the title compound (1.92 g, 100% yield).

Workup

  1. customThe excess iron was removed
  2. concentrationthe reaction mixture was concentrated under reduced pressure
  3. additionThe residue was diluted with EtOAc
  4. washsuccessively washed with water, aqueous saturated NaHCO3, and brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-9529d98fe90b463b802215cb8a1b3054
Source dataset
uspto-grants-2008_01
Patent number
US07323567B2

Reaction notes

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