N-(2-Hydroxyethyl)-4-nitrophthalimide → 5-Amino-2-(2-hydroxy-ethyl)-isoindole-1,3-dione

HRID 596756Notes

Reaction equation

HRID 596756 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]=1

Participants

5

Reactant 2

HCID 554768N-(2-Hydroxyethyl)-4-nitrophthalimideHCID 178418361HCID 178418361, compound

Product 1

HCID 7452975-Amino-2-(2-hydroxy-ethyl)-isoindole-1,3-dione

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

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

  1. filtrationThe hot solution is filtered
  2. customto remove the Raney nickel
  3. customthe solvent evaporated

Sources & evidence

ORD record
ord-fcf0a85fd0404e8fae621773a21e2910
Source dataset
uspto-grants-1977_03
Patent number
US04012372

Reaction notes

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