Sulfuric Acid → Methyl 3-amino-5-hydroxy-4-iodobenzoate

HRID 502366

Reaktionsgleichung

Reaktionsgleichung von HRID 502366
[NH2:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([OH:12])[C:10]=1[I:11])[C:5]([OH:7])=[O:6].S(=O)(=O)(O)O.[C:18](=O)([O-])O.[Na+]>CO>[CH3:18][O:6][C:5](=[O:7])[C:4]1[CH:8]=[C:9]([OH:12])[C:10]([I:11])=[C:2]([NH2:1])[CH:3]=1

Komponenten

5

Edukt 3

HCID 1118Sulfuric AcidHCID 516892Sodium BicarbonateHCID 684584523-Amino-5-hydroxy-4-iodobenzoic acid

Produkt 1

HCID 68458438Methyl 3-amino-5-hydroxy-4-iodobenzoateAusbeute 33 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

To a solution of 3-amino-5-hydroxy-4-iodo-benzoic acid (0.20 g, 0.72 mmol) in methanol (5 mL) was added conc. sulfuric acid (0.20 mL, 0.035 g, 0.36 mmol) and the reaction mixture heated to reflux. After 2 h, the reaction mixture was poured on ice, the pH adjusted to 9 by addition of a sat. solution of sodium hydrogencarbonate and extracted with ethyl acetate (2×50 mL). The combined organic phases were dried over MgSO4, concentrated by evaporation under reduced pressure and the crude material purified with column chromatography on silica eluting with hexane/ethyl acetate (1:1) providing 0.07 g (33%) of the title compound.

Aufarbeitung

  1. temperaturethe reaction mixture heated to reflux
  2. additionthe reaction mixture was poured on ice
  3. extractionextracted with ethyl acetate (2×50 mL)
  4. dry with materialThe combined organic phases were dried over MgSO4
  5. concentrationconcentrated by evaporation under reduced pressure
  6. customthe crude material purified with column chromatography on silica eluting with hexane/ethyl acetate (1:1)

Quellen und Nachweise

ORD-Eintrag
ord-8a1d1ab2ad7448f7bb43a9a4376fe837
Quelldatensatz
uspto-grants-2010_08
Patentnummer
US07772253B2

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