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

HRID 1672217Notes

Reaction equation

HRID 1672217 reaction equation
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]

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
70 °C

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-a663f48506b94ddf8c4235563cfe5c0c
Source dataset
uspto-grants-2011_08
Patent number
US07998952B2

Reaction notes

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