Hydrochloric Acid → Methyl 2-acetamidoisonicotinate

HRID 2186046

Reaktionsgleichung

Reaktionsgleichung von HRID 2186046
[C:1]([NH:4][C:5]1[CH:10]=[C:9]([C:11]([OH:13])=[O:12])[CH:8]=[CH:7][N:6]=1)(=[O:3])[CH3:2].Cl.[CH3:15]O>>[C:1]([NH:4][C:5]1[CH:10]=[C:9]([C:11]([O:13][CH3:15])=[O:12])[CH:8]=[CH:7][N:6]=1)(=[O:3])[CH3:2]

Komponenten

4

Edukt 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 37744662-Acetamidopyridine-4-carboxylic acid

Produkt 1

HCID 22185175Methyl 2-acetamidoisonicotinateAusbeute 84 %

Versuchsvorschrift

To 2-(acetamido)pyridine-4-carboxylic acid (25 g, 139 mmol) was added a saturated solution of anhydrous hydrogen chloride in methanol (600 mL). The cloudy suspension was stirred for 16 h at RT and refluxed for 24 h. The resulting solution was concentrated, dissolved in chloroform, washed with saturated sodium bicarbonate, brine, dried (magnesium sulfate) and concentrated to give the title compound as a white solid (17.86 g, 84%). TLC Rf 0.55 (5% methanol/chloroform); 1H NMR (CDCl3) δ3.96 (3H, s), 4.80 (2H, s),7.12 (1H, J=5 Hz, d), 7.19 (1H, s), 8.10 (1H, d, J=5 Hz).

Aufarbeitung

  1. temperaturerefluxed for 24 h
  2. concentrationThe resulting solution was concentrated
  3. dissolutiondissolved in chloroform
  4. washwashed with saturated sodium bicarbonate, brine
  5. dry with materialdried (magnesium sulfate)
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-ac748b9e140541a98c86945c2dde49df
Quelldatensatz
uspto-grants-2002_06
Patentnummer
US06403578B1

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