Ethyl Acetate → 2-(3-Amino-4-methyl-benzyl)-isoindole-1,3-dione

HRID 1454289Notes

Reaction equation

HRID 1454289 reaction equation
C[CH:2]([N:12]1[C:20](=[O:21])[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:13]1=[O:22])[C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([N+:9]([O-])=O)[CH:4]=1.[C:23](OCC)(=O)C>>[NH2:9][C:5]1[CH:4]=[C:3]([CH:8]=[CH:7][C:6]=1[CH3:23])[CH2:2][N:12]1[C:13](=[O:22])[C:14]2[C:19](=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:20]1=[O:21]

Participants

3

Reactant 2

HCID 8857Ethyl AcetateHCID 223935242-(Methyl-3-nitro-benzyl)-isoindole-1,3-dione

Product 1

HCID 223935232-(3-Amino-4-methyl-benzyl)-isoindole-1,3-dione

Procedure

2-(Methyl-3-nitro-benzyl)-isoindole-1,3-dione (0.45 g, 1.52 mmol) was taken up in ethyl acetate in a Paar vessel and flushed with argon. Palladium on carbon (100 mg) was added and the argon atmosphere was replaced with hydrogen at 50 psi. The vessel was shaken for 12 h. The hydrogen was then replaced with argon and the catalyst was removed by filtration through celite. The solvent was removed under reduced pressure to yield 0.40 g of the desired amine. C16H14N2O2 MS m/e=267.3 (M+H).

Workup

  1. customflushed with argon
  2. additionPalladium on carbon (100 mg) was added
  3. customthe catalyst was removed by filtration through celite
  4. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-00909c10e7e543a89f980a971ad5fedc
Source dataset
uspto-grants-2009_01
Patent number
US07479495B2

Reaction notes

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