1-(3,3-Dimethyl-6-nitroindolin-1-yl)ethanone → 1-(6-Amino-3,3-dimethylindolin-1-yl)ethanone

HRID 546563Notes

Reaction equation

HRID 546563 reaction equation
[C:1]([N:4]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([N+:13]([O-])=O)[CH:11]=2)[C:6]([CH3:17])([CH3:16])[CH2:5]1)(=[O:3])[CH3:2]>[Pd].C(O)C>[C:1]([N:4]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([NH2:13])[CH:11]=2)[C:6]([CH3:17])([CH3:16])[CH2:5]1)(=[O:3])[CH3:2]

Participants

4

Reactant 1

HCID 161274181-(3,3-Dimethyl-6-nitroindolin-1-yl)ethanone

Product 1

HCID 218651761-(6-Amino-3,3-dimethylindolin-1-yl)ethanoneYield 89.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

1.46 g of 10% palladium on charcoal, 8.8 g of 1-acetyl-3,3-dimethyl-6-nitroindoline obtained in stage e) below and 110 mL of ethanol are placed in a hydrogenation reactor. After reacting for one hour 10 minutes at 3 bar at a temperature of 25° C., the reaction medium is filtered through paper and concentrated under reduced pressure to give 6.9 g of 1-acetyl-3,3-dimethylindolin-6-amine in the form of a brown solid, the characteristics of which are as follows:

Workup

  1. filtrationthe reaction medium is filtered through paper
  2. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-7732807f52e041bc9522699f7a5babb2
Source dataset
uspto-grants-2011_05
Patent number
US07935819B2

Reaction notes

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