4-nitro-N-ethylphthalimide → 5-Amino-2-ethylisoindoline-1,3-dione

HRID 2288128

Reaction equation

[N+:1]([C:4]1[CH:5]=[C:6]2[C:11](=[O:12])[N:10]([CH2:13][CH3:14])[C:8](=[O:9])[C:7]2=[CH:15][CH:16]=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]([CH2:13][CH3:14])[C:8](=[O:9])[C:7]2=[CH:15][CH:16]=1

Participants

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 2.2 g of 4-nitro-N-ethylphthalimide. After displacing the air with nitrogen, the latter is replaced by hydrogen at atmospheric pressure and the suspension is stirred at 65° C. for 42 hours. During this time, 95% of the theoretical amount of hydrogen, based on the 4-nitro-N-ethylphthalimide, 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 250 ml of water. Drying at 80° C. under reduced pressure (125 mbar) gives 1.6 g (84%) of 4-amino-N-ethylphthalimide.

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 250 ml of water
customDrying at 80° C. under reduced pressure (125 mbar)

Sources & evidence

ORD record: ord-f07a7023e17a40659fa8378fbe3edb75
Source dataset: uspto-grants-2000_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06087480

Linked notes

Loading…