Methanol → Methyl 5-methoxy-1H-pyrrolo[2,3-C]pyridine-2-carboxylate

HRID 245773Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 245773
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[CH:11]=[C:10]([C:12]([OH:14])=[O:13])[NH:9][C:6]2=[CH:7][N:8]=1.S(=O)(=O)(O)O.[CH3:20]O>S(=O)(=O)(O)O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[CH:11]=[C:10]([C:12]([O:14][CH3:20])=[O:13])[NH:9][C:6]2=[CH:7][N:8]=1

Komponenten

5

Edukt 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 177504195-Methoxy-1H-pyrrolo[2,3-c]pyridine-2-carboxylic acid

Produkt 1

HCID 49759101Methyl 5-methoxy-1H-pyrrolo[2,3-C]pyridine-2-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1118Sulfuric AcidKatalysator

Versuchsvorschrift

To 5-methoxy-1H-pyrrolo[2,3-c]pyridine-2-carboxylic acid (1 g, 5.20 mmol) in methanol (100 ml) was added sulfuric acid (0.014 ml, 0.260 mmol). The resulting solution was heated to reflux and stirred at this temperature overnight. Then extra sulfuric acid (0.277 ml, 5.20 mmol) was added and heated at reflux for five days. The heating was stopped and the reaction mixture was concentrated to a smaller volume. The resulting suspension was diluted with ethyl acetate and washed with an aqueous saturated sodium hydrogen carbonate solution. The aqueous layer was extracted twice with ethyl acetate. The combined organic layers were washed with brine, dried (Na2SO4) and concentrated in vacuo to give methyl 5-methoxy-1H-pyrrolo[2,3-c]pyridine-2-carboxylate (910 mg).

Aufarbeitung

  1. temperatureThe resulting solution was heated
  2. temperatureto reflux
  3. temperatureheated
  4. temperatureat reflux for five days
  5. concentrationthe reaction mixture was concentrated to a smaller volume
  6. additionThe resulting suspension was diluted with ethyl acetate
  7. washwashed with an aqueous saturated sodium hydrogen carbonate solution
  8. extractionThe aqueous layer was extracted twice with ethyl acetate
  9. washThe combined organic layers were washed with brine
  10. dry with materialdried (Na2SO4)
  11. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-e11d1ae1f0e049ca844fcc4324b54185
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08658794B2

Notizen zur Reaktion

Wird geladen…