N-(2-Hydroxyethyl)-4-nitrophthalimide → 5-Amino-2-(2-hydroxy-ethyl)-isoindole-1,3-dione
Reaction equation
[OH:1][CH2:2][CH2:3][N:4]1[C:8](=[O:9])[C:7]2=[CH:10][C:11]([N+:14]([O-])=O)=[CH:12][CH:13]=[C:6]2[C:5]1=[O:17].[H][H]>[Ni].C(O)C>[NH2:14][C:11]1[CH:10]=[C:7]2[C:8](=[O:9])[N:4]([CH2:3][CH2:2][OH:1])[C:5](=[O:17])[C:6]2=[CH:13][CH:12]=1Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Procedure
N-(2-Hydroxyethyl)-4-nitrophthalimide (30.0 g.), ethanol (300 ml.), and Raney nickel (3.0 g.) are mixed and hydrogenated at 100°C. and 1500 psi. until hydrogen uptake ceases. The hot solution is filtered to remove the Raney nickel and the solvent evaporated to yield 4-amino-N-(2-hydroxyethyl)-phthalimide, the amine which melts at 171°-173°C.
Workup
- filtrationThe hot solution is filtered
- customto remove the Raney nickel
- customthe solvent evaporated
Sources & evidence
- ORD record
- ord-d3b80d0d84f644a4ac94b7fa26725b29
- Source dataset
- uspto-grants-1976_09
- Patent number
- US03980634
Reaction notes
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