1H-Isoindole-1,3(2H)-dione, 2-(4-nitrophenyl)- → 2-(4-Aminophenyl)-1H-isoindole-1,3(2H)-dione

HRID 2288135Notes

Reaction equation

HRID 2288135 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([N:10]2[C:14](=[O:15])[C:13]3=[CH:16][CH:17]=[CH:18][CH:19]=[C:12]3[C:11]2=[O:20])=[CH:6][CH:5]=1)([O-])=O.[H][H]>N.O[V](=O)=O.[O-2].[O-2].[Ti+4].[Pd].O>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([N:10]2[C:14](=[O:15])[C:13]3=[CH:16][CH:17]=[CH:18][CH:19]=[C:12]3[C:11]2=[O:20])=[CH:8][CH:9]=1

Participants

7

Reactant 2

HCID 1013141H-Isoindole-1,3(2H)-dione, 2-(4-nitrophenyl)-HCID 178418361HCID 178418361, compound

Product 1

HCID 6171382-(4-Aminophenyl)-1H-isoindole-1,3(2H)-dioneYield 80%

Reagents, catalysts & solvents 4

HCID 23938PalladiumCatalystHCID 62684Ammonium metavanadate [UN2859] [Poison]CatalystHCID 162651Titanium oxide (Ti3O)CatalystHCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

0.002 g of ammonium vanadate and 2 g of titanium dioxide extrudate containing 1% by weight of palladium and having a particle size of 3 mm (from Johnson Matthey) are added to a suspension consisting of 250 ml of water and 13.3 g of N-(4-nitrophenyl)phthalimide. After displacing the air with nitrogen, the latter is replaced by hydrogen at atmospheric pressure and the suspension is stirred at 60° C. At a hydrogen absorption of 40% of theory (after 42 hours), the suspension is transferred to an autoclave together with a catalyst and is then stirred at 100° C. under a hydrogen pressure of 10 bar for another 21 hours. During this time, a total of 115% of the theoretical amount of hydrogen, based on N-(4-nitrophenyl)phthalimide, is absorbed. After cooling to room temperature, the resulting suspension is sieved through a sieve having a mesh width of 1 mm. The material remaining on the sieve is washed with 50 ml of water and the combined aqueous phases are then filtered through a paper filter and washed with 250 ml of water. Drying at 80° C. under reduced pressure (125 mbar) gives 9.4 g (80%) of N-(4-aminophenyl)phthalimide.

Workup

  1. additionare added to a suspension
  2. customAt a hydrogen absorption of 40% of theory (after 42 hours)
  3. stirringis then stirred at 100° C. under a hydrogen pressure of 10 bar for another 21 hours
  4. customis absorbed
  5. temperatureAfter cooling to room temperature
  6. filtrationthe resulting suspension is sieved through a sieve
  7. washis washed with 50 ml of water
  8. filtrationthe combined aqueous phases are then filtered through a paper
  9. filtrationfilter
  10. washwashed with 250 ml of water
  11. customDrying at 80° C. under reduced pressure (125 mbar)

Sources & evidence

ORD record
ord-887c66a226e54d59bc0ecb6cb4bbc472
Source dataset
uspto-grants-2000_07
Patent number
US06087480

Reaction notes

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