4-Nitro-N-methylphthalimide → 5-amino-2-methyl-2,3-dihydro-1H-isoindole-1,3-dione
Reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:11](=[O:12])[N:10]([CH3:13])[C:8](=[O:9])[C:7]2=[CH:14][CH:15]=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]([CH3:13])[C:8](=[O:9])[C:7]2=[CH:14][CH:15]=1Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 4
Conditions
- Temperature
- 63 °C
Procedure
0.005 g of ammonium vanadate and 2.5 g 1% by weight of titanium dioxide extrudate containing metallic palladium and having a particle size of 3 mm (from Johnson Matthey) are added to a suspension consisting of 250 ml of water and 10.3 g of 4-nitro-N-methylphthalimide. After displacing the air with nitrogen, the latter is replaced by hydrogen at atmospheric pressure and the suspension is stirred at 63° C. for 75 hours. During this time, 104% of the theoretical amount of hydrogen, based on the 4-nitro-N-methylphthalimide, 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 50 ml of water. Drying at 80° C. under reduced pressure (125 mbar) gives 8.3 g (94%) of 4-amino-N-methylphthalimide. The purity determined by high pressure liquid chromatography is 98%.
Workup
- additionare added to a suspension
- customis absorbed
- filtrationThe resulting suspension is then sieved through a sieve
- washis washed with 50 ml of water
- filtrationthe combined aqueous phases are then filtered through a paper
- filtrationfilter
- washwashed with 50 ml of water
- customDrying at 80° C. under reduced pressure (125 mbar)
Sources & evidence
- ORD record
- ord-2747e8139f0944d19ea951627c277af8
- Source dataset
- uspto-grants-2000_07
- Patent number
- US06087480
Reaction notes
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