Methanol → Methyl 6-methylpyridine-2-carboxylate

HRID 643774

Reaktionsgleichung

Reaktionsgleichung von HRID 643774
[CH3:1][C:2]1[N:7]=[C:6]([C:8]([OH:10])=[O:9])[CH:5]=[CH:4][CH:3]=1.S(=O)(=O)(O)O.[CH3:16]O>>[CH3:16][O:9][C:8]([C:6]1[CH:5]=[CH:4][CH:3]=[C:2]([CH3:1])[N:7]=1)=[O:10]

Komponenten

4

Edukt 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 702826-Methylpyridine-2-carboxylic acid

Produkt 1

HCID 73022Methyl 6-methylpyridine-2-carboxylateAusbeute 59 %

Versuchsvorschrift

A mixture of 6-methyl-pyridine-2-carboxylic acid (10 g, 72.9 mmol) and concentrated sulfuric acid (3.5 mL) in methanol (300 mL) was heated at reflux overnight. The reaction mixture was cooled to room temperature and concentrated under reduced pressure. The residue was poured into saturated aqueous sodium hydrogen carbonate (250 mL), and extracted with ethyl acetate (3×100 mL). The combined organic layers were dried (magnesium sulfate), filtered, and evaporated to give 6-methyl-pyridine-2-carboxylic acid methyl ester (6.5 g, 59%) as a colorless oil. 1HNMR (CDCl3): δ 7.97 (d, J=7.6 Hz, 1H), 7.73 (dd, J=7.6 Hz, 1H), 7.36 (d, J=7.6 Hz, 1H), 4.01 (s, 3H), 2.67 (s, 3H).

Aufarbeitung

  1. temperaturewas heated
  2. temperatureat reflux overnight
  3. concentrationconcentrated under reduced pressure
  4. additionThe residue was poured into saturated aqueous sodium hydrogen carbonate (250 mL)
  5. extractionextracted with ethyl acetate (3×100 mL)
  6. dry with materialThe combined organic layers were dried (magnesium sulfate)
  7. filtrationfiltered
  8. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-81858029d6b741388925c417aa43d252
Quelldatensatz
uspto-grants-2010_04
Patentnummer
US07700632B2

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