HCID 22393544, compound → HCID 22393533, compound

HRID 1071522Notes

Reaction equation

HRID 1071522 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[N+:11]([O-])=O)[C:7](=[O:14])[NH:6][CH2:5]2>C(OCC)(=O)C>[NH2:11][C:10]1[CH:9]=[C:8]2[C:4]([CH2:5][NH:6][C:7]2=[O:14])=[CH:3][C:2]=1[CH3:1]

Participants

3

Reactant 1

HCID 22393544HCID 22393544, compound

Product 1

HCID 22393533HCID 22393533, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

5-Methyl-6-nitro-2,3-dihydro-isoindol-1-one (100.00 mg, 0.52 mmol) was taken up in ethyl acetate in a Paar vessel and flushed with argon. Palladium on carbon (25 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 65.8 mg of the desired amine. C9H10N2O MS m/e=163.2 (M+H).

Workup

  1. customflushed with argon
  2. additionPalladium on carbon (25 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-cc4fa0ef5f1744418518e2d38bfd1209
Source dataset
uspto-grants-2005_06
Patent number
US06906067B2

Reaction notes

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