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

HRID 1275007Notes

Reaction equation

HRID 1275007 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]>C1COCC1.[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 95%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A stirred suspension of 1-acetyl-2,3-dihydro-6-nitro-1H-indole (D9, 125 g, 0.61 mole) in THF (5500 ml) was hydrogenated over 10% Pd-C (20 g) at 50 psi for 20 h. The catalyst was removed by filtration through a plug of kieselguhr and the filtrate concentrated in vacuo to afford the title compound as a beige solid (102 g, 95%).

Workup

  1. customThe catalyst was removed by filtration through a plug of kieselguhr
  2. concentrationthe filtrate concentrated in vacuo

Sources & evidence

ORD record
ord-cf38a93b1ec34dc4aa53d5c96bcf3c32
Source dataset
uspto-grants-2000_12
Patent number
US06159979

Reaction notes

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