3,3-Dimethyl-6-nitro-1,3-dihydro-2H-indol-2-one → 6-Amino-3,3-dimethyl-1,3-dihydro-2H-indol-2-one

HRID 535364Notes

Reaction equation

HRID 535364 reaction equation
[CH3:1][C:2]1([CH3:15])[C:10]2[C:5](=[CH:6][C:7]([N+:11]([O-])=O)=[CH:8][CH:9]=2)[NH:4][C:3]1=[O:14]>[Pd].CO>[NH2:11][C:7]1[CH:6]=[C:5]2[C:10]([C:2]([CH3:15])([CH3:1])[C:3](=[O:14])[NH:4]2)=[CH:9][CH:8]=1

Participants

4

Reactant 1

HCID 135892273,3-Dimethyl-6-nitro-1,3-dihydro-2H-indol-2-one

Product 1

HCID 135892296-Amino-3,3-dimethyl-1,3-dihydro-2H-indol-2-oneYield 68.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 3,3-dimethyl-6-nitroindolin-2-one (1.2 g, 5.8 mmol) (Mertens et al, J. Med. Chem. 30:1279, 1987), 10% Pd—C (100 mg), and MeOH (100 mL) was stirred under hydrogen atmosphere (1 atm) for 10 h. The catalyst was filtered out and the filtrate was concentrated. The residue was purified by column to give an off-white solid (700 mg).

Workup

  1. filtrationThe catalyst was filtered out
  2. concentrationthe filtrate was concentrated
  3. customThe residue was purified by column

Sources & evidence

ORD record
ord-544fe810917842be884216b055a5c960
Source dataset
uspto-grants-2014_10
Patent number
US08859545B2

Reaction notes

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