5-nitro-2,3-dihydro-1H-isoindol-1-one → 5-Amino-2,3-dihydro-isoindol-1-one

HRID 1487209

Reaction equation

HRID 1487209 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[C:9](=[O:13])[NH:8][CH2:7]2)([O-])=O>CO.[Pd]>[NH2:1][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[C:9](=[O:13])[NH:8][CH2:7]2

Participants

4

Reactant 1

HCID 140056255-nitro-2,3-dihydro-1H-isoindol-1-one

Product 1

HCID 219562395-Amino-2,3-dihydro-isoindol-1-oneYield 76.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 5-nitroisoindolin-1-one (60 mg, 0.337 mmol) in methanol (20 mL) was added palladium on carbon (10%, 50 mg). The mixture was stirred under an atmosphere of hydrogen for 1 hour. Filtration through Celite, followed by concentration led to 5-aminoisoindolin-1-one as a tan solid (38 mg, yield 76.2%).

Workup

  1. filtrationFiltration through Celite
  2. concentrationfollowed by concentration

Sources & evidence

ORD record
ord-556d76abfbfe4db791622751ece56d35
Source dataset
uspto-grants-2016_08
Patent number
US09428508B2

Linked notes

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