1-Acetyl-7-nitro-5-ethoxycarbonylmethyl-4,6-dimethylindoline → 1-Acetyl-7-amino-5-ethoxycarbonylmethyl-4,6-dimethylindoline

HRID 1744041Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1744041
[C:1]([N:4]1[C:12]2[C:7](=[C:8]([CH3:23])[C:9]([CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])=[C:10]([CH3:16])[C:11]=2[N+:13]([O-])=O)[CH2:6][CH2:5]1)(=[O:3])[CH3:2]>[Pd].C(O)C>[C:1]([N:4]1[C:12]2[C:7](=[C:8]([CH3:23])[C:9]([CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])=[C:10]([CH3:16])[C:11]=2[NH2:13])[CH2:6][CH2:5]1)(=[O:3])[CH3:2]

Komponenten

4

Edukt 1

HCID 121122001-Acetyl-7-nitro-5-ethoxycarbonylmethyl-4,6-dimethylindoline

Produkt 1

HCID 121122011-Acetyl-7-amino-5-ethoxycarbonylmethyl-4,6-dimethylindoline

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
55 °C

Versuchsvorschrift

In a 100-ml autoclave, 1-acetyl-7-nitro-5-ethoxycarbonylmethyl-4,6-dimethylindoline (5.0 g) obtained in Example 5 and 7.5% palladium on charcoal (wet, 3.76 g) were suspended in ethanol (50 ml). After degassing with nitrogen for 3 times (5 kg/cm2 for each) and replacing nitrogen with hydrogen for 3 times (5 kg/cm2 for each) successively, the resulting mixture was stirred for 2 hours at 55° C. under a pressurized hydrogen atmosphere (5 kg/cm2). The reaction mixture was filtered to remove palladium on charcoal, which was washed with ethanol (50 ml). The filtrate and washing were combined and concentrated under reduced pressure to give a fraction of the title compound. Furthermore, palladium on charcoal separated above was suspended in dichloromethane (50 ml), and after stirring at room temperature, the catalyst was removed by filtration and washed with dichloromethane (25 ml). The filtrate and washing were combined and concentrated under reduced pressure to give another fraction of the title compound. The title compound (4.1 g, yield: 90%) was obtained by combining two fractions of the title compound obtained above.

Aufarbeitung

  1. customAfter degassing with nitrogen for 3 times (5 kg/cm2 for each) and
  2. filtrationThe reaction mixture was filtered
  3. customto remove palladium on charcoal, which
  4. washwas washed with ethanol (50 ml)
  5. washThe filtrate and washing
  6. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-4516a270416f4b779fffe20c444ab141
Quelldatensatz
uspto-grants-2006_03
Patentnummer
US07012147B2

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