Ammonium formate → 4-AMINOISOINDOLIN-1-ONE

HRID 1525629Notes

Reaction equation

HRID 1525629 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+]>CO.[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-one

Product 1

HCID 98555134-AMINOISOINDOLIN-1-ONEYield 92%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Conditions

Temperature
35 °C

Procedure

A mixture of 4-nitro-2,3-dihydro-1H-isoindol-1-one (20 g), ammonium formate (35 g) and 7.5% Pd/C (0.6 g) in methanol (60 ml) was stirred for 2 hours by heating up to 35° C. Pd/C was filtered and the filtrate concentrated under reduced pressure. The residue was recrystallized from water to give 15.3 g of light yellow solid. yield: 92%. mp: 195.6-197° C.

Workup

  1. filtrationPd/C was filtered
  2. concentrationthe filtrate concentrated under reduced pressure
  3. customThe residue was recrystallized from water
  4. customto give 15.3 g of light yellow solid

Sources & evidence

ORD record
ord-ace2a51603bc43feb12ac5b518b8ad47
Source dataset
uspto-grants-2015_07
Patent number
US09085530B2

Reaction notes

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