HCID 4017380, compound → HCID 22501979, compound

HRID 2288130Notes

Reaction equation

HRID 2288130 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:11](=[O:12])[N:10]([CH:13]([CH3:15])[CH3:14])[C:8](=[O:9])[C:7]2=[CH:16][CH:17]=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]=[C:6]2[C:11](=[O:12])[N:10]([CH:13]([CH3:15])[CH3:14])[C:8](=[O:9])[C:7]2=[CH:16][CH:17]=1

Participants

7

Reactant 2

HCID 4017380HCID 4017380, compound2×HCID 178418361HCID 178418361, compound2×

Product 1

HCID 22501979HCID 22501979, compoundYield 59.8%

Reagents, catalysts & solvents 4

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

Conditions

Temperature
65 °C

Procedure

0.001 g of ammonium vanadate and 0.5 g of titanium dioxide extrudate containing 1% by weight of metallic palladium and having a particle size of 3 mm (from Johnson Matthey) are added to a suspension consisting of 50 ml of water and 2.3 g of 4-nitro-N-isopropylphthalimide. After displacing the air with nitrogen, the latter is replaced by hydrogen at atmospheric pressure and the suspension is stirred at 65° C. for 71 hours. During this time, 102% of the theoretical amount of hydrogen, based on the 4-nitro-N-isopropylphthalimide, 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 50 ml of water and the combined aqueous phases are then filtered through a paper filter and washed with 1000 ml of water. Drying at 80° C. under reduced pressure (125 mbar) gives 1.2 g (57%) of 4-amino-N-isopropylphthalimide.

Workup

  1. additionare added to a suspension
  2. customis absorbed
  3. filtrationThe resulting suspension is then sieved through a sieve
  4. washis washed with 50 ml of water
  5. filtrationthe combined aqueous phases are then filtered through a paper
  6. filtrationfilter
  7. washwashed with 1000 ml of water
  8. customDrying at 80° C. under reduced pressure (125 mbar)

Sources & evidence

ORD record
ord-f56f5de0a38c4c21901d180874efa31d
Source dataset
uspto-grants-2000_07
Patent number
US06087480

Reaction notes

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