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

HRID 1805042Notes

Reaction equation

HRID 1805042 reaction equation
[CH3:1][C:2]1([CH3:17])[C:10]2[C:5](=[CH:6][C:7]([N+:11]([O-])=O)=[CH:8][CH:9]=2)[N:4]([C:14](=[O:16])[CH3:15])[CH2:3]1>CO.[Pd]>[NH2:11][C:7]1[CH:6]=[C:5]2[C:10]([C:2]([CH3:17])([CH3:1])[CH2:3][N:4]2[C:14](=[O:16])[CH3:15])=[CH:9][CH:8]=1

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 70.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

10% Pd—C (0.2 g) was added to a suspension of 1-(3,3-dimethyl-6-nitroindolin-1-yl)ethanone (2.1 g, 9 mmol) in MeOH (20 mL). The reaction was stirred under H2 (40 psi) at room temperature overnight. Pd—C was filtered off and the filtrate was concentrated under vacuum to give a crude product, which was purified by column chromatography to yield 1-(6-amino-3,3-dimethyl-2,3-dihydro-indol-1-yl)-ethanone (DC-8) (1.3 g, 61%).

Workup

  1. filtrationPd—C was filtered off
  2. concentrationthe filtrate was concentrated under vacuum
  3. customto give a crude product, which
  4. customwas purified by column chromatography

Sources & evidence

ORD record
ord-5eb60cbbc66745fc9b67b1bb347697c2
Source dataset
uspto-grants-2013_01
Patent number
US08354427B2

Reaction notes

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