Sodium Hydroxide → 6-Methoxy-5-methylpyridin-2-amine

HRID 1772913Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1772913
[OH-].[Na+].[CH3:3][O:4][C:5]1[N:10]=[C:9]([NH:11]C(=O)C)[CH:8]=[CH:7][C:6]=1[CH3:15]>CO.O>[CH3:3][O:4][C:5]1[N:10]=[C:9]([NH2:11])[CH:8]=[CH:7][C:6]=1[CH3:15]

Komponenten

5

Edukt 2

HCID 14798Sodium HydroxideHCID 90030978N-(6-methoxy-5-methylpyridin-2-yl)acetamide2×

Produkt 1

HCID 900221706-Methoxy-5-methylpyridin-2-amineAusbeute 194,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

A 10% solution of aqueous NaOH (40 mL) was added to a solution of N-(6-methoxy-5-methylpyridin-2-yl)acetamide (2.21 g, 12.3 mmol) in MeOH (160 mL) and the reaction mixture was heated at 90° C. for 3 d. After cooling to rt and concentration in vacuo to remove the MeOH the aqueous residue was combined with that from a previous batch derived from N-(6-methoxy-5-methylpyridin-2-yl)acetamide (2.21 g, 12.3 mmol). The aqueous phase was diluted with H2O (40 mL) and extracted with DCM (3×150 mL). The combined organic phases were washed with brine, dried (Na2SO4) and combined with a previous batch of crude 6-methoxy-5-methylpyridin-2-amine (266 mg). Concentration in vacuo yielded the title compound (3.30 g, 23.9 mmol).

Aufarbeitung

  1. temperatureAfter cooling to rt
  2. concentrationconcentration in vacuo
  3. customto remove the MeOH the aqueous residue
  4. extractionextracted with DCM (3×150 mL)
  5. washThe combined organic phases were washed with brine
  6. dry with materialdried (Na2SO4)
  7. concentrationConcentration in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-4a2b32b1f6ce4e7ca2ec7bd9a4bff329
Quelldatensatz
uspto-grants-2016_02
Patentnummer
US09249160B2

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