4-Nitro-N-methylphthalimide → 5-amino-2-methyl-2,3-dihydro-1H-isoindole-1,3-dione

HRID 2236724

Reaction equation

HRID 2236724 reaction equation
[CH3:1][N:2]1[C:10](=[O:11])[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([N+:12]([O-])=O)[CH:8]=2)[C:3]1=[O:15]>C(O)C.O1CCCC1.[Ni]>[NH2:12][C:7]1[CH:8]=[C:9]2[C:4](=[CH:5][CH:6]=1)[C:3](=[O:15])[N:2]([CH3:1])[C:10]2=[O:11]

Participants

4

Reactant 1

HCID 923214-Nitro-N-methylphthalimide

Product 1

HCID 7269315-amino-2-methyl-2,3-dihydro-1H-isoindole-1,3-dione

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 21873804Tetrahydrofuran ethanolSolvent

Procedure

A solution of give 2-methyl-5-nitro-isoindole-1,3-dione (1.1 g, 5.3 mmol) in ethanol/tetrahydrofuran (1:1, 50 mL) is hydrogenated at 45 psi over Raney nickel catalyst. The reaction mixture is filtered through a pad of diatomaceous earth and concentrated to give 5-amino-2-methyl-isoindole-1,3-dione as a yellow cottony solid (0.85 g, 91%).

Workup

  1. filtrationThe reaction mixture is filtered through a pad of diatomaceous earth
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-e3ae9f82d5b44b96b1a0bff5d36b5d7a
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Linked notes

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