ethyl 5-(2-methoxyethoxy)-7-nitro-1H-indole-2-carboxylate → ethyl 7-amino-5-(2-methoxyethoxy)-1H-indole-2-carboxylate

HRID 1960378Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1960378
[CH3:1][O:2][CH2:3][CH2:4][O:5][C:6]1[CH:7]=[C:8]2[C:12](=[C:13]([N+:15]([O-])=O)[CH:14]=1)[NH:11][C:10]([C:18]([O:20][CH2:21][CH3:22])=[O:19])=[CH:9]2>[C].[Pd].O1CCCC1>[NH2:15][C:13]1[CH:14]=[C:6]([O:5][CH2:4][CH2:3][O:2][CH3:1])[CH:7]=[C:8]2[C:12]=1[NH:11][C:10]([C:18]([O:20][CH2:21][CH3:22])=[O:19])=[CH:9]2

Komponenten

4

Edukt 1

HCID 57476190ethyl 5-(2-methoxyethoxy)-7-nitro-1H-indole-2-carboxylate

Produkt 1

HCID 57476192ethyl 7-amino-5-(2-methoxyethoxy)-1H-indole-2-carboxylateAusbeute 99,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418390HCID 178418390, VerbindungKatalysatorHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A mixture of ethyl 5-(2-methoxyethoxy)-7-nitro-1H-indole-2-carboxylate (2.30 g), 10% palladium carbon (50% containing water, 500 mg) and tetrahydrofuran (100 mL) was subjected to catalytic reduction at room temperature under hydrogen atmosphere at normal pressure. The catalyst was removed by filtration, and the filtrate was concentrated. The residue was washed with hexane to give the title compound (2.07 g, yield 99%) as pale-brown crystals. The crystals were recrystallized from ethyl acetate-hexane to give pale-brown prism crystals. melting point 162-163° C.

Aufarbeitung

  1. customwas subjected to catalytic reduction at room temperature under hydrogen atmosphere at normal pressure
  2. customThe catalyst was removed by filtration
  3. concentrationthe filtrate was concentrated
  4. washThe residue was washed with hexane

Quellen und Nachweise

ORD-Eintrag
ord-a1861580ec9a4d25b1457b2789c2e727
Quelldatensatz
uspto-grants-2013_04
Patentnummer
US08410087B2

Notizen zur Reaktion

Wird geladen…