Methyl iodide → HCID 68527240, compound

HRID 1932445Notes

Reaction equation

HRID 1932445 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([O:10][C:11]2[CH:16]=[CH:15][C:14]([CH2:17][C:18]([O:20][CH3:21])=[O:19])=[CH:13][CH:12]=2)=[N:8][CH:9]=1)([O-:3])=[O:2].[H-].[Na+].[CH3:24]I.[Cl-].[NH4+]>CN(C=O)C>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([O:10][C:11]2[CH:16]=[CH:15][C:14]([CH:17]([CH3:24])[C:18]([O:20][CH3:21])=[O:19])=[CH:13][CH:12]=2)=[N:8][CH:9]=1)([O-:3])=[O:2]

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 16797620HCID 16797620, compound

Product 1

HCID 68527240HCID 68527240, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of methyl 2-[4-(5-nitropyridin-2-yloxy)phenyl]acetate (0.50 g, 1.7 mmol) in DMF (10 mL) were added 60% sodium hydride (0.153 g, 3.8 mmol) and methyl iodide (0.13 mL, 2.1 mmol), and the resulting reaction solution was stirred for 1 hour at 0° C. To the reaction solution was added saturated aqueous ammonium chloride, and extracted with ethyl acetate. The ethyl acetate layer was washed with water and saturated aqueous sodium chloride. The ethyl acetate layer was dried over anhydrous magnesium sulfate, evaporated, and the residue was purified by silica gel chromatography (n-hexane:ethyl acetate=8:1), to thereby yield 0.32 g of the title compound.

Workup

  1. customthe resulting reaction solution
  2. extractionextracted with ethyl acetate
  3. washThe ethyl acetate layer was washed with water and saturated aqueous sodium chloride
  4. dry with materialThe ethyl acetate layer was dried over anhydrous magnesium sulfate
  5. customevaporated
  6. customthe residue was purified by silica gel chromatography (n-hexane:ethyl acetate=8:1)

Sources & evidence

ORD record
ord-6b7a70cfc9174ede847d26a587462636
Source dataset
uspto-grants-2012_05
Patent number
US08188277B2

Reaction notes

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