Stannous chloride dihydrate → Methyl 7-aminobenzofuran-4-carboxylate

HRID 354054Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 354054
O.O.[Sn](Cl)Cl.[CH3:6][O:7][C:8]([C:10]1[CH:11]=[CH:12][C:13]([N+:19]([O-])=O)=[C:14]2[O:18][CH:17]=[CH:16][C:15]=12)=[O:9]>C(OCC)(=O)C.C(O)C>[CH3:6][O:7][C:8]([C:10]1[CH:11]=[CH:12][C:13]([NH2:19])=[C:14]2[O:18][CH:17]=[CH:16][C:15]=12)=[O:9]

Komponenten

5

Edukt 2

HCID 61436Stannous chloride dihydrateHCID 20738655Methyl 7-nitrobenzofuran-4-carboxylate

Produkt 1

HCID 14939320Methyl 7-aminobenzofuran-4-carboxylateAusbeute 88,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

Tin (II) chloride dihydrate (15.0 g, 66.5 mmol) was added to a suspension of 7-nitro-benzofuran-4-carboxylic acid methyl ester (4.82 g, 21.8 mmol) in ethyl acetate (80 mL) and ethanol (80 mL). The reaction mixture was stirred at room temperature for four days then partitioned between ethyl acetate and saturated aqueous solution of potassium carbonate. The organic extract was washed with brine, dried (anhydrous sodium sulfate) and concentrated under reduced pressure. The residue was purified by flash column chromatography over silica gel eluting with 30% ethyl acetate in hexane give 7-amino-benzofuran-4-carboxylic acid methyl ester (3.67 g, 88%). 1H NMR (CDCl3) δ: 3.92 (s, 3H), 6.60 (d, 1H, J=8.2 Hz), 7.34 (d, 1H, J=2.1 Hz), 7.67 (d, 1H, J=2.1 Hz), 7.84 (d, 1H, J=8.2 Hz).

Aufarbeitung

  1. customthen partitioned between ethyl acetate and saturated aqueous solution of potassium carbonate
  2. extractionThe organic extract
  3. washwas washed with brine
  4. dry with materialdried (anhydrous sodium sulfate)
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by flash column chromatography over silica gel eluting with 30% ethyl acetate in hexane

Quellen und Nachweise

ORD-Eintrag
ord-552ff75ebe944761a6c6c026da337dcb
Quelldatensatz
uspto-grants-2004_06
Patentnummer
US06756395B2

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