Ammonium formate → 4-AMINOISOINDOLIN-1-ONE

HRID 1862085Notes

Reaction equation

HRID 1862085 reaction equation
[N+:1]([C:4]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:5]=1[CH2:6][NH:7][C:8]2=[O:13])([O-])=O.C([O-])=O.[NH4+]>CN(C=O)C.[Pd]>[NH2:1][C:4]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:5]=1[CH2:6][NH:7][C:8]2=[O:13]

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 219613874-Nitro-2,3-dihydro-1H-isoindol-1-one2×

Product 1

HCID 98555134-AMINOISOINDOLIN-1-ONEYield 82,492.297%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 4-nitro-2,3-dihydro-1H-isoindol-1-one (compound 3, 3.2 gm, 0.018 mmol.) in DMF (10 ml), was added ammonium formate (5.750 gm), and Pd—C (100 mg), and the reaction mixture was stirred at 100° C. for 30 min. The mixture was then filtered through a pad of celite, and the celite was washed with DMF (10 ml) and water (10 ml). The filtrate was concentrated under vacuum to give compound 4 (2.2 gm, 83%).

Workup

  1. filtrationThe mixture was then filtered through a pad of celite
  2. washthe celite was washed with DMF (10 ml) and water (10 ml)
  3. concentrationThe filtrate was concentrated under vacuum

Sources & evidence

ORD record
ord-f3e419f77b904a33bc8cfe6cc60576dd
Source dataset
uspto-grants-2003_03
Patent number
US06534651B2

Reaction notes

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