p-Fluoronitrobenzene → HCID 7062386, compound

HRID 1713808Notes

Reaction equation

HRID 1713808 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=1.[CH3:11][C@H:12]1[O:17][C@@H:16]([CH3:18])[CH2:15][NH:14][CH2:13]1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH3:18][C@H:16]1[O:17][C@@H:12]([CH3:11])[CH2:13][N:14]([C:2]2[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=2)[CH2:15]1

Participants

5

Reactant 3

HCID 9590p-FluoronitrobenzeneHCID 11430Potassium CarbonateHCID 6415002,6-Dimethylmorpholine, cis-

Product 1

HCID 7062386HCID 7062386, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

1-Fluoro-4-nitrobenzene (4.9 g, 34.75 mmol) was added to a stirred mixture of cis-2,6-dimethylmorpholine (44.4 g, 38.26 mmol) and anhydrous potassium carbonate (2.5 g, 18.12 mmol) in acetonitrile (50 mL). The mixture was heated under reflux for 19 h, cooled, filtered and the solid washed with acetonitrile. The filtrate was concentrated by evaporation to give the title compound (8.1 g, 99%) as a solid; 1H NMR δ (CDCl3): 8.13 (2H, d), 6.82 (2H, d), 3.76 (2H, m), 3.66 (2H, dt), 2.61 (2H, t), 1.28 (6H, d); MS m/e MH+: 237.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 19 h
  3. temperaturecooled
  4. filtrationfiltered
  5. washthe solid washed with acetonitrile
  6. concentrationThe filtrate was concentrated by evaporation

Sources & evidence

ORD record
ord-a46cf8cfed1844fcb4039d4757171f49
Source dataset
uspto-grants-2010_09
Patent number
US07795283B2

Reaction notes

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