Water → 5-[(2-Methoxypyridin-4-yl)oxy]-N-methyl-2-nitroaniline

HRID 1843715Notes

Reaction equation

HRID 1843715 reaction equation
F[C:2]1[CH:3]=[CH:4][C:5]([N+:10]([O-:12])=[O:11])=[C:6]([CH:9]=1)[NH:7][CH3:8].[CH3:13][O:14][C:15]1[CH:20]=[C:19]([OH:21])[CH:18]=[CH:17][N:16]=1.C(=O)([O-])[O-].[Cs+].[Cs+].O>CN(C=O)C>[CH3:13][O:14][C:15]1[CH:20]=[C:19]([O:21][C:2]2[CH:3]=[CH:4][C:5]([N+:10]([O-:12])=[O:11])=[C:6]([CH:9]=2)[NH:7][CH3:8])[CH:18]=[CH:17][N:16]=1

Participants

6

Reactant 4

HCID 962WaterHCID 10796Cesium carbonateHCID 229057745-fluoro-N-methyl-2-nitroanilineHCID 178493525HCID 178493525, compound

Product 1

HCID 667057615-[(2-Methoxypyridin-4-yl)oxy]-N-methyl-2-nitroanilineYield 66%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 5-fluoro-N-methyl-2-nitroaniline (US2003-675927, 3.30 g, 19.4 mmol), 2-methoxypyridin-4-ol (2.70 g, 21.6 mmol) produced in Example (16b) and cesium carbonate (10.6 g, 32.4 mmol) in DMF (20 mL) was stirred at 80° C. for two hours. After leaving to cool, water (100 mL) was added to the reaction mixture, followed by extraction with ethyl acetate (100 mL). The organic layer was washed with water (100 mL) twice and dried over anhydrous sodium sulfate. After concentration under reduced pressure, the residue was purified by silica gel chromatography (hexane/ethyl acetate, 2:1) to obtain the title compound (3.90 g, 66%) as a yellow solid.

Workup

  1. customAfter leaving
  2. temperatureto cool
  3. extractionfollowed by extraction with ethyl acetate (100 mL)
  4. washThe organic layer was washed with water (100 mL) twice
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationAfter concentration under reduced pressure
  7. customthe residue was purified by silica gel chromatography (hexane/ethyl acetate, 2:1)

Sources & evidence

ORD record
ord-5398403fbce74639be7494c23c6e9808
Source dataset
uspto-grants-2015_02
Patent number
US08946264B2

Reaction notes

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