Hydrochloric Acid → 3,6-Dichloro-5-trifluoromethyl-2-pyridone

HRID 464131Notes

Reaction equation

HRID 464131 reaction equation
[OH-:1].[K+].[Cl:3][C:4]1[C:9]([Cl:10])=[CH:8][C:7]([C:11]([F:14])([F:13])[F:12])=[C:6]([Cl:15])[N:5]=1.Cl>C(O)(C)(C)C>[Cl:10][C:9]1[C:4](=[O:1])[NH:5][C:6]([Cl:15])=[C:7]([C:11]([F:14])([F:13])[F:12])[CH:8]=1.[Cl:10][C:9]1[CH:8]=[C:7]([C:11]([F:14])([F:13])[F:12])[C:6](=[O:1])[NH:5][C:4]=1[Cl:3]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 27606902,3,6-Trichloro-5-(trifluoromethyl)pyridine

Product 2

HCID 134917763,6-Dichloro-5-trifluoromethyl-2-pyridoneHCID 134917775,6-Dichloro-3-trifluoromethyl-2-pyridone

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

To a solution of 2.7 g of potassium hydroxide dissolved in 37 ml of t-butanol was added 6.0 g of 2,3,6-trichloro-5-trifluoromethylpyridine, and the solution was reacted at 80° C. for 3 hours while stirring. After completion of the reaction, the reaction product was allowed to cool and made acidic with concentrated hydrochloric acid. The solvent was distilled off under reduced pressure, and the residue was extracted with methylene chloride. The methylene chloride solution was washed with water and dried over anhydrous sodium sulfate. The methylene chloride was distilled off under reduced pressure, and the resulting residue was passed through a silica gel column (eluent: an n-hexane-ethyl acetate (3:1 by weight) mixture) to obtain 1.5 g of 3,6-dichloro-5-trifluoromethyl-2-pyridone having a melting point of 129° to 131° C. and 0.8 g of 5,6-dichloro-3-trifluoromethyl-2-pyridone having a melting point of 163° to 165° C., respectively.

Workup

  1. customthe solution was reacted at 80° C. for 3 hours
  2. customAfter completion of the reaction
  3. temperatureto cool
  4. distillationThe solvent was distilled off under reduced pressure
  5. extractionthe residue was extracted with methylene chloride
  6. washThe methylene chloride solution was washed with water
  7. dry with materialdried over anhydrous sodium sulfate
  8. distillationThe methylene chloride was distilled off under reduced pressure

Sources & evidence

ORD record
ord-c73373fb0e594425b6e2b10ff428bd3d
Source dataset
uspto-grants-1985_10
Patent number
US04546191

Reaction notes

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