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 971254Notes

Reaction equation

HRID 971254 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 99.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 3,3-dimethyl-6-nitroindolin-2-one (500 mg, 2.4 mmol), 10% Pd—C (100 mg), and MeOH (100 mL) was stirred under H2 (1 atm) for 3 h. After that the catalyst was filtered off and the filtrate was concentrated to give an off-white solid (420 mg).

Workup

  1. filtrationAfter that the catalyst was filtered off
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-7821239df1d54127a3fe52258941be94
Source dataset
uspto-grants-2007_12
Patent number
US07312330B2

Reaction notes

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