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

HRID 502196

Reaction equation

HRID 502196 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) is suspended in EtOAc (200 mL). Pd/C (650 mg, 10%) is added, and the mixture is hydrogenated at 40-55 p.s.i. for 2 hours. The mixture is then filtered through celite. The filtrate is concentrated, and the residue is triturated with ether to yield 1-acetyl-6-aminoindoline (3.18 g, 99%) as an orange solid.

Workup

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

Sources & evidence

ORD record
ord-3176c00d69924d3187679b4c09e95813
Source dataset
uspto-grants-2010_08
Patent number
US07772271B2

Linked notes

Loading…