Morpholine → 4-(6-Methyl-5-nitro-2-pyridinyl)morpholine

HRID 2388008

Reaktionsgleichung

Reaktionsgleichung von HRID 2388008
F[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[C:4]([CH3:11])[N:3]=1.[NH:12]1[CH2:17][CH2:16][O:15][CH2:14][CH2:13]1.C(=O)([O-])[O-].[K+].[K+]>CS(C)=O>[CH3:11][C:4]1[N:3]=[C:2]([N:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)[CH:7]=[CH:6][C:5]=1[N+:8]([O-:10])=[O:9]

Komponenten

5

Edukt 3

HCID 8083MorpholineHCID 11430Potassium CarbonateHCID 124081856-Fluoro-2-methyl-3-nitropyridine

Produkt 1

HCID 82089554-(6-Methyl-5-nitro-2-pyridinyl)morpholineAusbeute 99 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

To a solution of 2-fluoro-5-nitro-6-picoline (3.0 g, 19.2 mmol) in DMSO (26 mL) were added morpholine (3.35 mL, 38.4 mmol) and potassium carbonate (6.64 g, 48.0 mmol). The reaction mixture was allowed to stir overnight, at 70° C. The reaction mixture was then partitioned between EtOAc (40 mL) and water (40 mL). The organic solution was separated and the aqueous solution was extracted with EtOAc (2×40 mL). The organic solutions were combined, washed with brine, dried over MgSO4, filtered and concentrated to give 4-(6-methyl-5-nitropyridin-2-yl)morpholine (4.0 g, 99%), as a muddy green solid. LCMS (FA): Rt=1.59 min, m/z=224.0 (M+H).

Aufarbeitung

  1. customThe reaction mixture was then partitioned between EtOAc (40 mL) and water (40 mL)
  2. customThe organic solution was separated
  3. extractionthe aqueous solution was extracted with EtOAc (2×40 mL)
  4. washwashed with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-06856b0ed9c843d68bf56fab76e05399
Quelldatensatz
uspto-grants-2012_09
Patentnummer
US08268992B2

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