Water → HCID 67335196, compound

HRID 451478Notes

Reaction equation

HRID 451478 reaction equation
Br[C:2]1[C:3]([N+:8]([O-:10])=[O:9])=[N:4][CH:5]=[CH:6][CH:7]=1.[C:11](=[O:14])([O-])[O-].[K+].[K+].O>CS(C)=O.[I-].C([N+](CCCC)(CCCC)CCCC)CCC>[N+:8]([C:3]1[C:2]([N:4]2[CH2:5][CH2:11][O:14][CH2:2][CH2:3]2)=[CH:7][CH:6]=[CH:5][N:4]=1)([O-:10])=[O:9]

Participants

6

Reactant 3

HCID 962WaterHCID 11430Potassium CarbonateHCID 5940443-Bromo-2-nitropyridine

Product 1

HCID 67335196HCID 67335196, compound

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of 3-bromo-2-nitropyridine (207 mg, 1 mmol) in DMSO (2 mL) was added at room temperature under stirring and under an atmosphere of nitrogen morpholine (95.8 mg, 95.8 μL, 1.1 mmol), tetrabutyl ammonium iodide (18.5 mg, 50.0 μmol) and potassium carbonate (152 mg, 1.1 mmol). The reaction was stirred at 80° C. over night. Water was added and the aqueous phase was extracted twice with diethyl ether. The combined organic layers were washed with water and with saturated aqueous sodium chloride solution, dried over sodium sulfate, filtered and the solvent was evaporated under reduced pressure. The title compound was obtained as a yellow oil (57 mg, 27%) after column chromatography on silica gel using a gradient from heptane/ethyl acetate 4:1 to 1:1 (v/v) as eluent.

Workup

  1. stirringThe reaction was stirred at 80° C. over night
  2. extractionthe aqueous phase was extracted twice with diethyl ether
  3. washThe combined organic layers were washed with water and with saturated aqueous sodium chloride solution
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-ee5cb0fc8364487ea44ee373efc8780b
Source dataset
uspto-grants-2013_07
Patent number
US08486967B2

Reaction notes

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