7-Nitrooxindole → 7-Aminoindolin-2-one

HRID 1844103Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1844103
[N+:1]([C:4]1[CH:5]=[CH:6][CH:7]=[C:8]2[C:12]=1[NH:11][C:10](=[O:13])[CH2:9]2)([O-])=O.[H][H]>CO.[Pd]>[NH2:1][C:4]1[CH:5]=[CH:6][CH:7]=[C:8]2[C:12]=1[NH:11][C:10](=[O:13])[CH2:9]2

Komponenten

5

Edukt 2

HCID 64248387-NitrooxindoleHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 64233127-Aminoindolin-2-one

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 887MethanolLösungsmittel

Versuchsvorschrift

To a solution of 7-nitroindoline-2-one in methanol (1.0 gm/60 mL), added Pd/C (300 mg, 30 wt %). H2 gas maintained with pressure using hydrogen gas balloon, solution stirred for 4 hours at RT. The catalyst was removed by filtration over celite. The filtrate was concentrated in vacuo to give crude product, which was washed with diethyl ether to afford compound 7-aminoindolin-2-one; YD: 76.77%; mp: 248-251° C.; Rf: 0.6 (CHCl3:MeOH: 9.0:1.0). 1H NMR (DMSO-d6) 200 MHz, δ: 3.382 (s, 2H), 4.794 (s, 2H), 6.453-6.498 (m, 2H), 6.673 (t, J=8.0 Hz, 1H), 9.906 (s, 1H). MS (ESI): m/z 146.8 [M−H]−.

Aufarbeitung

  1. temperatureH2 gas maintained with pressure
  2. customThe catalyst was removed by filtration over celite
  3. concentrationThe filtrate was concentrated in vacuo
  4. customto give crude product, which
  5. washwas washed with diethyl ether

Quellen und Nachweise

ORD-Eintrag
ord-e8b9700d77af4eed8d017d91d79917ea
Quelldatensatz
uspto-grants-2015_02
Patentnummer
US08946282B2

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