Sodium Methoxide → 2-(4-Chloro-3-methoxyphenyl)-5-trifluoromethyl-3-methoxypyridine

HRID 1957248Notes

Reaction equation

HRID 1957248 reaction equation
[CH3:1][O-:2].[Na+].Cl[C:5]1[C:6]([C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[C:17]([O:22][CH3:23])[CH:16]=2)=[N:7][CH:8]=[C:9]([C:11]([F:14])([F:13])[F:12])[CH:10]=1>CO>[Cl:21][C:18]1[CH:19]=[CH:20][C:15]([C:6]2[C:5]([O:2][CH3:1])=[CH:10][C:9]([C:11]([F:14])([F:13])[F:12])=[CH:8][N:7]=2)=[CH:16][C:17]=1[O:22][CH3:23]

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 157668763-Chloro-2-(4-chloro-3-methoxyphenyl)-5-trifluoromethylpyridine

Product 1

HCID 190687532-(4-Chloro-3-methoxyphenyl)-5-trifluoromethyl-3-methoxypyridine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

33.5 g of a 30% strength methanolic solution of sodium methoxide were added to a solution of 3.0 g (9.3 mmol) of 3-chloro-2-(4-chloro-3-methoxyphenyl)-5-trifluoromethylpyridine in 100 ml of methanol. The mixture was refluxed for 20 h and then poured into about 500 ml of ice-water. The product was extracted from the aqueous phase with 3×100 ml of methylene chloride. The combined organic phases were dried over sodium sulfate and concentrated. The oily residue was induced to crystallize by trituration with n-hexane. Yield: 1.3 g of colorless crystals; melting point: 62°-63° C. (purity about 85%).

Workup

  1. temperatureThe mixture was refluxed for 20 h
  2. extractionThe product was extracted from the aqueous phase with 3×100 ml of methylene chloride
  3. dry with materialThe combined organic phases were dried over sodium sulfate
  4. concentrationconcentrated
  5. customto crystallize by trituration with n-hexane

Sources & evidence

ORD record
ord-5edf00fcfbbf4590a10dd035f89322ec
Source dataset
uspto-grants-1998_07
Patent number
US05783522

Reaction notes

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