Ethyl 5-nitro-1-benzothiophene-2-carboxylate → Ethyl 5-amino-1-benzothiophene-2-carboxylate

HRID 500677Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 500677
[CH2:1]([O:3][C:4]([C:6]1[S:10][C:9]2[CH:11]=[CH:12][C:13]([N+:15]([O-])=O)=[CH:14][C:8]=2[CH:7]=1)=[O:5])[CH3:2]>CCO.[Pd]>[CH2:1]([O:3][C:4]([C:6]1[S:10][C:9]2[CH:11]=[CH:12][C:13]([NH2:15])=[CH:14][C:8]=2[CH:7]=1)=[O:5])[CH3:2]

Komponenten

4

Edukt 1

HCID 737499Ethyl 5-nitro-1-benzothiophene-2-carboxylate

Produkt 1

HCID 2764450Ethyl 5-amino-1-benzothiophene-2-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 702EthanolLösungsmittel

Versuchsvorschrift

A suspension of 5-nitro-benzo[b]thiophene-2-carboxylic acid ethyl ester (10.52 g, 41.89 mmol) and 10% Pd/C (1.1 g) in 450 mL of EtOH was hydrogenated under 1 atm of H12 for 4 d at rt. The reaction mixture was filtered and the filtrate was concentrated and dried to give 5-amino-benzo[b]thiophene-2-carboxylic acid ethyl ester as a green solid. A parallel reaction was preformed on 10.61 g of 5-nitro-benzo[b]thiophene-2-carboxylic acid ethyl ester in the same manner. A total of 18.37 g of 5-amino-benzo[b]thiophene-2-carboxylic acid ethyl ester was obtained. MS (EI): cal'd 222.0 (MH+), exp 222.2 (MH+).

Aufarbeitung

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate was concentrated
  3. customdried

Quellen und Nachweise

ORD-Eintrag
ord-616ebaaefd7546e7a29d80154544ff40
Quelldatensatz
uspto-grants-2010_08
Patentnummer
US07772238B2

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