4-Nitrophthalimide → 4-Aminophthalimide

HRID 2288126Notes

Reaction equation

HRID 2288126 reaction equation
[O-2].[Al+3].[O-2].[O-2].[Al+3].[N+:6]([C:9]1[CH:10]=[C:11]2[C:16](=[O:17])[NH:15][C:13](=[O:14])[C:12]2=[CH:18][CH:19]=1)([O-])=O.[H][H].[N+](C1C=CC=C2C(NC(=O)C=12)=O)([O-])=O>N.O[V](=O)=O.[Pd].O>[NH2:6][C:9]1[CH:10]=[C:11]2[C:16](=[O:17])[NH:15][C:13](=[O:14])[C:12]2=[CH:18][CH:19]=1

Participants

8

Reactant 4

HCID 69694-NitrophthalimideHCID 117793-NitrophthalimideHCID 9989226AluminaHCID 178418361HCID 178418361, compound2×

Product 1

HCID 729154-AminophthalimideYield 99%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 62684Ammonium metavanadate [UN2859] [Poison]CatalystHCID 962WaterSolvent

Procedure

0.002 g of ammonium vanadate and 4 g of aluminium oxide granules containing 0.5% by weight of metallic palladium and having a particle size of 3.2 mm (as in Ex. 1) are added to a suspension consisting of 250 ml of water and 9.6 g of 4-nitrophthalimide. After displacing the air with nitrogen, the latter is replaced by hydrogen at atmospheric pressure and the suspension is stirred at room temperature for 20 hours. During this time, 100.6% of the theoretical amount of hydrogen, based on the nitrophthalimide used, is absorbed. The resulting suspension is then sieved through a sieve having a mesh width of 1 mm. The residue remaining on the sieve is washed with water and the combined aqueous phases are subsequently filtered through a paper filter. Drying at 80° C. under reduced pressure (125 mbar) gives 8.0 g (99%) of 4-aminophthalimide.

Workup

  1. additionare added to a suspension
  2. customis absorbed
  3. filtrationThe resulting suspension is then sieved through a sieve
  4. washis washed with water
  5. filtrationthe combined aqueous phases are subsequently filtered through a paper
  6. filtrationfilter
  7. customDrying at 80° C. under reduced pressure (125 mbar)

Sources & evidence

ORD record
ord-f5ae9ce686a44fa4ba3d0965b51e6047
Source dataset
uspto-grants-2000_07
Patent number
US06087480

Reaction notes

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