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

HRID 2253304Notes

Reaction equation

HRID 2253304 reaction equation
[Br:1]Br.[NH2:3][C:4]1[C:13]([N+:14]([O-:16])=[O:15])=[C:12]2[C:7]([C:8]([CH3:20])([CH3:19])[C:9](=[O:18])[NH:10][C:11]2=[O:17])=[CH:6][CH:5]=1>CC(O)=O>[NH2:3][C:4]1[C:13]([N+:14]([O-:16])=[O:15])=[C:12]2[C:7]([C:8]([CH3:20])([CH3:19])[C:9](=[O:18])[NH:10][C:11]2=[O:17])=[CH:6][C:5]=1[Br:1]

Participants

4

Reactant 2

HCID 24408BromineHCID 111184431,3(2H,4H)-Isoquinolinedione, 7-amino-4,4-dimethyl-8-nitro-

Product 1

HCID 596454677-amino-6-bromo-4,4-dimethyl-8-nitroisoquinoline-1,3(2H,4H)-dioneYield 99%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
25 °C

Procedure

Bromine (9.27 mL, 188.6 mmol) was added dropwise to a solution of 7-amino-4,4-dimethyl-8-nitroisoquinoline-1,3(2H,4H)-dione (4.70 g, 18.86 mmol) in AcOH (190 mL). The reaction mixture was stirred at 25° C. for 2 h then was concentrated under reduced pressure. The residue was diluted with EtOAc, and successively washed with water, aqueous saturated NaHCO3, aqueous saturated Na2S2O3, and brine, dried (MgSO4), filtered and concentrated under reduced pressure to give the title compound (6.10 g, 99% yield).

Workup

  1. concentrationthen was concentrated under reduced pressure
  2. additionThe residue was diluted with EtOAc
  3. washsuccessively washed with water, aqueous saturated NaHCO3, aqueous saturated Na2S2O3, and brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-647a532ce59142d0bbcb553cf64876ce
Source dataset
uspto-grants-2008_01
Patent number
US07323567B2

Reaction notes

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