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

HRID 1576296

Reaction equation

HRID 1576296 reaction equation
[CH2:1]([N:3]1[C:7](=[O:8])[C:6]2=[CH:9][C:10]([N+:13]([O-])=O)=[CH:11][CH:12]=[C:5]2[C:4]1=[O:16])[CH3:2]>[Ni].C(O)C>[NH2:13][C:10]1[CH:9]=[C:6]2[C:7](=[O:8])[N:3]([CH2:1][CH3:2])[C:4](=[O:16])[C:5]2=[CH:12][CH:11]=1

Participants

4

Reactant 1

HCID 8404084-nitro-N-ethylphthalimide

Product 1

HCID 187040545-Amino-2-ethylisoindoline-1,3-dione

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

N-Ethyl-4-nitrophthalimide (28.0 g.) is hydrogenated in 400 ml. of ethanol and in the presence of Raney nickel catalyst (10 g.) at 100°C. and 1500 psi. pressure. The reaction mixture is filtered to remove the catalyst and the filtrate is concentrated to yield the product, 4-amino-N-ethylphthalimide, which is recrystallized from methanol-water mixture. It melts at 169°-171°C.

Workup

  1. customat 100°C.
  2. filtrationThe reaction mixture is filtered
  3. customto remove the catalyst
  4. concentrationthe filtrate is concentrated

Sources & evidence

ORD record
ord-df09496caaff4101b31cd073e0fd018d
Source dataset
uspto-grants-1976_09
Patent number
US03980634

Linked notes

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