Methyl 4-iodo-3-nitrobenzoate → Methyl 3-amino-4-iodobenzoate

HRID 400603

Reaktionsgleichung

Reaktionsgleichung von HRID 400603
[CH3:1][O:2][C:3](=[O:14])[C:4]1[CH:9]=[CH:8][C:7]([I:10])=[C:6]([N+:11]([O-])=O)[CH:5]=1>C(O)(=O)C.[Fe]>[CH3:1][O:2][C:3](=[O:14])[C:4]1[CH:9]=[CH:8][C:7]([I:10])=[C:6]([NH2:11])[CH:5]=1

Komponenten

4

Edukt 1

HCID 297884Methyl 4-iodo-3-nitrobenzoate

Produkt 1

HCID 21628210Methyl 3-amino-4-iodobenzoateAusbeute 88,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23925IronKatalysatorHCID 176Acetic AcidLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A solution of 4-iodo-3-nitrobenzoic acid methyl ester (2.0 g, 6.50 mmol) in 25 mL of absolute alcohol and 15 mL of glacial acetic acid was treated with iron powder (3.6 g, 65.0 mmol) and the mixture was heated at 80° C. After 1 hour, the reaction mixture was filtered through a pad of silica, washed with ethanol, and concentrated in vacuo. The residue was diluted with a solution of potassium carbonate and extracted with ethyl acetate. The combined organic layers were washed with brine, dried over sodium sulfate, filtered, and concentrated in vacuo to give 1.6 g of 3-amino-4-iodobenzoic acid methyl ester as a white solid (88% yield).

Aufarbeitung

  1. filtrationthe reaction mixture was filtered through a pad of silica
  2. washwashed with ethanol
  3. concentrationconcentrated in vacuo
  4. additionThe residue was diluted with a solution of potassium carbonate
  5. extractionextracted with ethyl acetate
  6. washThe combined organic layers were washed with brine
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-7d5b4f8cd506480dacb0dc38b550ddf1
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08741897B2

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