1-(6-Nitroindolin-1-yl)ethanone → 1-Acetyl-6-aminoindoline

HRID 907178

Reaction equation

HRID 907178 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)[CH2:6][CH2:5]1)(=[O:3])[CH3:2]>CCOC(C)=O.[Pd]>[C:1]([N:4]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([NH2:13])[CH:11]=2)[CH2:6][CH2:5]1)(=[O:3])[CH3:2]

Participants

4

Reactant 1

HCID 2585661-(6-Nitroindolin-1-yl)ethanone

Product 1

HCID 2585641-Acetyl-6-aminoindolineYield 99%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

1-Acetyl-6-nitroindoline (3.8 g, 18.3 mmol) was suspended in EtOAc (200 mL). Pd/C (650 mg, 10%) was added, and the mixture was hydrogenated at 40-55 p.si.i. for 2 hours. The mixture was then filtered through celite. The filtrate was concentrated, and the residue was triturated with ether to yield 1-acetyl-6-aminoindoline (3.18 g, 99%) as an orange solid.

Workup

  1. filtrationThe mixture was then filtered through celite
  2. concentrationThe filtrate was concentrated
  3. customthe residue was triturated with ether

Sources & evidence

ORD record
ord-211f6a2e7df249da86df1b907705f7e8
Source dataset
uspto-grants-2011_09
Patent number
US08013006B2

Linked notes

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