Water → HCID 23503599, compound

HRID 1835402Notes

Reaction equation

HRID 1835402 reaction equation
[CH3:1][O-:2].[Na+].[CH3:4][O:5][C:6]1[C:24]([O:25][CH3:26])=[CH:23][C:9]([C:10]([C:12]2[C:13](Cl)=[N:14][CH:15]=[CH:16][C:17]=2[C:18]([F:21])([F:20])[F:19])=[O:11])=[C:8]([CH3:27])[CH:7]=1.O>C1(C)C=CC=CC=1>[CH3:4][O:5][C:6]1[C:24]([O:25][CH3:26])=[CH:23][C:9]([C:10]([C:12]2[C:13]([O:2][CH3:1])=[N:14][CH:15]=[CH:16][C:17]=2[C:18]([F:21])([F:20])[F:19])=[O:11])=[C:8]([CH3:27])[CH:7]=1

Participants

5

Reactant 3

HCID 962WaterHCID 10942334Sodium MethoxideHCID 23503587HCID 23503587, compound

Product 1

HCID 23503599HCID 23503599, compoundYield 100.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

0.9 g (16 mmol) of sodium methoxide was added to a solution having 1.5 g (4.2 mmol) of 3-(4,5-dimethoxy-2-methylbenzoyl)-2-chloro-4-trifluoromethylpyridine synthesized in accordance with a process in Synthesis Example 1 dissolved in 20 ml of toluene, followed by stirring under reflux by heating for 4 hours. The mixture was cooled, and then 20 ml of water was added thereto to terminate the reaction, the aqueous solution was extracted with ethyl acetate, and the organic layer was dried over anhydrous sodium sulfate and subjected to filtration by using a silica gel cake. The solvent was distilled off under reduced pressure to obtain 1.5 g (yield 99%) of 3-(4,5-dimethoxy-2-methylbenzoyl)-2-methoxy-4-trifluoromethylpyridine (compound No. 32; m.p. 125-127° C.).

Workup

  1. customsynthesized in accordance with a process in Synthesis Example 1
  2. temperatureunder reflux
  3. temperatureby heating for 4 hours
  4. temperatureThe mixture was cooled
  5. customto terminate
  6. customthe reaction
  7. extractionthe aqueous solution was extracted with ethyl acetate
  8. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  9. filtrationsubjected to filtration
  10. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-9a3fa1c5ea5548e48161d048a58a3d3e
Source dataset
uspto-grants-2004_08
Patent number
US06770662B2

Reaction notes

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