Ethyl 2-(5-fluoro-2-nitroanilino)benzo[b]thiophene-3-carboxylate → Ethyl 2-(2-amino-5-fluoroanilino)benzo[b]thiophene-3-carboxylate

HRID 1281767Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1281767
[F:1][C:2]1[CH:3]=[CH:4][C:5]([N+:23]([O-])=O)=[C:6]([CH:22]=1)[NH:7][C:8]1[S:12][C:11]2[CH:13]=[CH:14][CH:15]=[CH:16][C:10]=2[C:9]=1[C:17]([O:19][CH2:20][CH3:21])=[O:18].[H][H]>C(OCC)(=O)C.[C].[Pd]>[NH2:23][C:5]1[CH:4]=[CH:3][C:2]([F:1])=[CH:22][C:6]=1[NH:7][C:8]1[S:12][C:11]2[CH:13]=[CH:14][CH:15]=[CH:16][C:10]=2[C:9]=1[C:17]([O:19][CH2:20][CH3:21])=[O:18]

Komponenten

5

Edukt 2

HCID 18422317Ethyl 2-(5-fluoro-2-nitroanilino)benzo[b]thiophene-3-carboxylateHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 18422159Ethyl 2-(2-amino-5-fluoroanilino)benzo[b]thiophene-3-carboxylateAusbeute 52,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418390HCID 178418390, VerbindungKatalysatorHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

Ethyl 2-(5-fluoro-2-nitroanilino)benzo[b]thiophene-3-carboxylate (50.7 g) was dissolved in ethyl acetate (1000 ml) and 10% palladium-carbon (8.0 g) was added. The mixture was stirred with hydrogen (60 kg/cm2) at 55° C. for 5 hr. The reaction mixture was cooled and the catalyst was filtered off. The filtrate was evaporated under reduced pressure and the residue was purified by silica gel column chromatography (chloroform) to give ethyl 2-(2-amino-5-fluoroanilino)benzo[b]thiophene-3-carboxylate (24.5 g).

Aufarbeitung

  1. temperatureThe reaction mixture was cooled
  2. filtrationthe catalyst was filtered off
  3. customThe filtrate was evaporated under reduced pressure
  4. customthe residue was purified by silica gel column chromatography (chloroform)

Quellen und Nachweise

ORD-Eintrag
ord-abbbe6be5c2544dba8439acd6cc7da9f
Quelldatensatz
uspto-grants-2002_09
Patentnummer
US06455521B1

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