Water → 7-Amino-4-bromo-3-hydroxyisoindolinone

HRID 21088

Reaction equation

HRID 21088 reaction equation
[NH2:1][C:2]1[CH:12]=[CH:11][C:10]([Br:13])=[C:4]2[C:5]([NH:7][C:8](=[O:9])[C:3]=12)=[O:6].[H-].C([Al+]CC(C)C)C(C)C.O>C1COCC1>[NH2:1][C:2]1[CH:12]=[CH:11][C:10]([Br:13])=[C:4]2[C:3]=1[C:8](=[O:9])[NH:7][CH:5]2[OH:6]

Participants

5

Reactant 3

HCID 962WaterHCID 21225700DiisobutylaluminumhydrideHCID 684890894-amino-7-bromo-2,3-dihydro-1H-isoindole-1,3-dione

Product 1

HCID 684910457-Amino-4-bromo-3-hydroxyisoindolinoneYield 72.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3-Amino-6-bromophthalimide (3.10 g, 12.9 mmol) was dissolved in THF (240 mL), and the solution was added with diisobutylaluminiumhydride (0.94 mol/L, 68.6 mL, 64.5 mmol) by drops at −78° C. for 25 minutes, then the reaction mixture was warmed to room temperature, followed by stirring for 1.5 hours. Then, the reaction mixture was ice-cooled, added with water and filtered using Celite. The filtrate was extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by slurry using chloroform to obtain 7-amino-4-bromo-3-hydroxyisoindolinone (2.26 g, yield 72%).

Workup

  1. temperaturecooled
  2. filtrationfiltered
  3. extractionThe filtrate was extracted with ethyl acetate
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customThe residue was purified by slurry

Sources & evidence

ORD record
ord-07fff94954834be4b0ddba67b532291f
Source dataset
uspto-grants-2010_06
Patent number
US07745641B2

Linked notes

Loading…