Nitrosobenzene → 5-(3-Amino-benzoyl)-1,3-dihydro-indol-2-one

HRID 640816

Reaktionsgleichung

Reaktionsgleichung von HRID 640816
[N+:1]([C:4]1[CH:5]=[C:6]([CH:19]=[CH:20][CH:21]=1)[C:7]([C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[NH:14][C:13](=[O:18])[CH2:12]2)=[O:8])([O-])=O.O=NC1C=CC=CC=1.CO.C(Cl)(Cl)Cl>CO.[Pd]>[NH2:1][C:4]1[CH:5]=[C:6]([CH:19]=[CH:20][CH:21]=1)[C:7]([C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[NH:14][C:13](=[O:18])[CH2:12]2)=[O:8]

Komponenten

6

Edukt 3

HCID 11473NitrosobenzeneHCID 21584188Chloroform methanolHCID 686984765-(3-Nitro-benzoyl)-1,3-dihydro-indol-2-one

Produkt 1

HCID 644240015-(3-Amino-benzoyl)-1,3-dihydro-indol-2-one

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 887MethanolLösungsmittel

Versuchsvorschrift

5-(3-Nitro-benzoyl)-1,3-dihydro-indol-2-one (2.0 g, 7.09 mmol) was dissolved in MeOH (600 mL). 10% Pd/C (0.20 g) was added to the flask and then placed under vacuum to remove any O2(g). The reaction mixture was kept under reduced pressure for ˜5 min and was then charged with H2(g) at atmospheric pressure. This evacuation/H2(g) fill procedure was repeated twice. The reaction mixture was stirred for 2 h at which point the starting material had been completely consumed. As the desired ketone product was prone to over-reduction to the alcohol, stopping the reaction immediately upon complete consumption of the starting material limited the amount over-reduction that occurred. The reaction mixture was filtered over celite and the filtrate was concentrated in vacuo resulting in a solid that contained the desired keto-aniline product plus ˜5% of the overreduced alcohol-aniline. Flash silica gel chromatography (5% MeOH/CHCl3) of the crude solid provided pure 5-(3-Amino-benzoyl)-1,3-dihydro-indol-2-one in 72% (0.957 g, 3.80 mmol) yield.

Aufarbeitung

  1. customto remove any O2(g)
  2. additionwas then charged with H2(g) at atmospheric pressure
  3. customhad been completely consumed
  4. customthe reaction
  5. customimmediately upon complete consumption of the starting material
  6. filtrationThe reaction mixture was filtered over celite
  7. concentrationthe filtrate was concentrated in vacuo
  8. customresulting in a solid

Quellen und Nachweise

ORD-Eintrag
ord-39603ffa48544aa89dc76c98fbea4ec9
Quelldatensatz
uspto-grants-2010_04
Patentnummer
US07692005B2

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