Sodium Methoxide → 2-Methoxy-6-(2-methoxy-4-trifluoromethoxy-phenyl)-5-methyl-3-nitro-pyridine

HRID 2179999Notes

Reaction equation

HRID 2179999 reaction equation
[CH3:1][O-:2].[Na+].Cl[C:5]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][C:8]([CH3:14])=[C:7]([C:15]2[CH:20]=[CH:19][C:18]([O:21][C:22]([F:25])([F:24])[F:23])=[CH:17][C:16]=2[O:26][CH3:27])[N:6]=1>CO>[CH3:1][O:2][C:5]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][C:8]([CH3:14])=[C:7]([C:15]2[CH:20]=[CH:19][C:18]([O:21][C:22]([F:25])([F:24])[F:23])=[CH:17][C:16]=2[O:26][CH3:27])[N:6]=1

Participants

4

Reactant 2

HCID 10942334Sodium Methoxide2×HCID 224900592-Chloro-6-(2-methoxy-4-trifluoromethoxy-phenyl)-5-methyl-3-nitro-pyridine

Product 1

HCID 224900612-Methoxy-6-(2-methoxy-4-trifluoromethoxy-phenyl)-5-methyl-3-nitro-pyridine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent3×

Procedure

A solution of sodium methoxide in MeOH (14 ml, 25%, 60.7 mmol) is added to a solution of 2-chloro-6-(2-methoxy-4-trifluoromethoxy-phenyl)-5-methyl-3-nitro-pyridine (20 g, 55.14 mmol) in MeOH (170 ml) at room temperature. The mixture is refluxed for 8 hours. Additional sodium methoxide in MeOH (14 ml, 25%, 60.7 mmol) is added and refluxed for 15 hours. After cooling to room temperature, the mixture is concentrated under reduced pressure. Water (300 ml) is added to the concentrated mixture and the mixture is extracted with EtOAc. The combined extracts are washed with brine and dried over Na2SO4. The solvent is removed under reduced pressure and the residue is purified by flash column chromatography (hexane/EtOAc 20:1) to give 2-methoxy-6-(2-methoxy-4-trifluoromethoxy-phenyl)-5-methyl-3-nitro-pyridine as white solid. Rf (hexane/EtOAc=9:1)=0.32.

Workup

  1. temperatureThe mixture is refluxed for 8 hours
  2. temperaturerefluxed for 15 hours
  3. concentrationthe mixture is concentrated under reduced pressure
  4. additionWater (300 ml) is added to the concentrated mixture
  5. extractionthe mixture is extracted with EtOAc
  6. washThe combined extracts are washed with brine
  7. dry with materialdried over Na2SO4
  8. customThe solvent is removed under reduced pressure
  9. customthe residue is purified by flash column chromatography (hexane/EtOAc 20:1)

Sources & evidence

ORD record
ord-0f84c28bcb604ee4bd379d65c4f35b42
Source dataset
uspto-grants-2005_05
Patent number
US06887875B2

Reaction notes

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