Morpholine → Methyl 2-(morpholin-4-yl)pyridine-4-carboxylate

HRID 602378Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 602378
Cl[C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][N:11]=1)[C:5]([O:7][CH3:8])=[O:6].C(OCC)(=O)C.[NH:18]1[CH2:23][CH2:22][O:21][CH2:20][CH2:19]1>[Cl-].[Na+].O>[O:21]1[CH2:22][CH2:23][N:18]([C:2]2[CH:3]=[C:4]([CH:9]=[CH:10][N:11]=2)[C:5]([O:7][CH3:8])=[O:6])[CH2:19][CH2:20]1

Komponenten

5

Edukt 3

HCID 8083MorpholineHCID 8857Ethyl AcetateHCID 2736842Methyl 2-chloropyridine-4-carboxylate

Produkt 1

HCID 2762487Methyl 2-(morpholin-4-yl)pyridine-4-carboxylateAusbeute 98 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 57417360Sodium chloride; waterLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

Methyl 2-chloroisonicotinate (320 mg, 1.89 mmol) was dissolved in morpholine (5 mL) and stirred at 90° C. for 4 hours. The reaction mixture was added with saturated brine and ethyl acetate, and the organic layer was separated, followed by washing with saturated brine. The organic layer was dried over anhydrous magnesium sulfate and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane=1/4) to obtain methyl 2-morpholinoisonicotinate (50 mg, 98%).

Aufarbeitung

  1. customthe organic layer was separated
  2. washby washing with saturated brine
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane=1/4)

Quellen und Nachweise

ORD-Eintrag
ord-1f40cf3cefd44fb68ab4f6ad9bca8d43
Quelldatensatz
uspto-grants-2011_03
Patentnummer
US07906522B2

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