Methyl 3-iodo-4-methyl-5-nitrobenzoate → HCID 67512060, Verbindung

HRID 59801Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 59801
[CH3:1][O:2][C:3](=[O:15])[C:4]1[CH:9]=[C:8]([N+:10]([O-])=O)[C:7]([CH3:13])=[C:6]([I:14])[CH:5]=1>C1COCC1.CO>[CH3:1][O:2][C:3](=[O:15])[C:4]1[CH:5]=[C:6]([I:14])[C:7]([CH3:13])=[C:8]([NH2:10])[CH:9]=1

Komponenten

4

Edukt 1

HCID 24728110Methyl 3-iodo-4-methyl-5-nitrobenzoate

Produkt 1

HCID 67512060HCID 67512060, VerbindungAusbeute 67,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

To a solution of 3-iodo-4-methyl-5-nitro-benzoic acid methyl ester (2.0 g, 6.23 mmol) in a mixture of THF (40 mL) and methanol (1 mL) was added SnCl2 dihydrate (4.22 g, 18.69 mmol). The reaction mixture was stirred at 60° C. for six hours, then cooled to room temperature and partitioned between ethyl acetate and saturated aqueous sodium bicarbonate. The organic layer was separated, dried over MgSO4, filtered and concentrated under reduced pressure. The residue was purified by column chromatography to afford 1.22 g (67%) of 3-amino-5-iodo-4-methyl-benzoic acid methyl ester.

Aufarbeitung

  1. temperaturecooled to room temperature
  2. custompartitioned between ethyl acetate and saturated aqueous sodium bicarbonate
  3. customThe organic layer was separated
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-b8589116d89f46d6a9f73922539356cb
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09440956B2

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