4-Nitrophthalimide → 4-Aminophthalimide

HRID 2288125Notes

Reaction equation

HRID 2288125 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].CO>[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 100%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 62684Ammonium metavanadate [UN2859] [Poison]CatalystHCID 887MethanolSolvent

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 (from Acros Organics) are added to a suspension consisting of 250 ml of methanol 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 43 hours. During this time, 97.6% of the theoretical amount of hydrogen, based on the nitrophthalimide, is absorbed. The resulting suspension is then sieved through a sieve having a mesh width of 1 mm. The material remaining on the sieve is washed with methanol and the methanol is subsequently removed from the combined methanol phases by means of a rotary evaporator. Drying at 60° C. under reduced pressure (125 mbar) gives 8.1 g (100%) 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 methanol
  5. customthe methanol is subsequently removed from the combined methanol phases by means of a rotary evaporator
  6. customDrying at 60° C. under reduced pressure (125 mbar)

Sources & evidence

ORD record
ord-5258d3a409ed4e8ca4de7bc6b71230a7
Source dataset
uspto-grants-2000_07
Patent number
US06087480

Reaction notes

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