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 19641Notes

Reaction equation

HRID 19641 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-5901467b3c5a4059bdae7131e764f158
Source dataset
uspto-grants-2010_06
Patent number
US07745451B2

Reaction notes

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