Water → 7-Amino-4-bromo-2,3-dihydroisoindol-1-one

HRID 21089Notes

Reaction equation

HRID 21089 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([Br:13])=[C:6]2[C:10]=1[C:9](=[O:11])[NH:8][CH:7]2O.FC(F)(F)C(O)=O.C([SiH](CC)CC)C.O>[N+](C)([O-])=O>[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([Br:13])=[C:6]2[C:10]=1[C:9](=[O:11])[NH:8][CH2:7]2

Participants

6

Reactant 4

HCID 962WaterHCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 684910457-Amino-4-bromo-3-hydroxyisoindolinone

Product 1

HCID 197019327-Amino-4-bromo-2,3-dihydroisoindol-1-oneYield 74.3%

Reagents, catalysts & solvents 1

HCID 6375NitromethaneSolvent

Procedure

7-Amino-4-bromo-3-hydroxyisoindolinone (3.11 g, 12.8 mmol) was dissolved in nitromethane (125 mL), and the solution was added with trifluoroacetic acid (9.90 mL, 128 mmol) and triethylsilane (4.10 mL, 25.6 mmol), followed by stirring at room temperature for 2 hours. The reaction mixture was added with water, extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium hydrogencarbonate solution and saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by slurry using chloroform to obtain 7-amino-4-bromoisoindolinone (2.16 g, yield 74%).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with saturated aqueous sodium hydrogencarbonate solution and saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customthe residue was purified by slurry

Sources & evidence

ORD record
ord-dcddd7e42c624d299abe44804df57b43
Source dataset
uspto-grants-2010_06
Patent number
US07745641B2

Reaction notes

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