Hydrochloric Acid → 2,6-Dimethyl-4-trifluoromethylpyridine-3-carboxylic acid hydrochloride

HRID 2373678Notes

Reaction equation

HRID 2373678 reaction equation
[CH3:1][C:2]1[C:7]([C:8]([O:10]C)=[O:9])=[C:6]([C:12]([F:15])([F:14])[F:13])[CH:5]=[C:4]([CH3:16])[N:3]=1.[OH-].[K+].[ClH:19]>C(O)C>[ClH:19].[CH3:1][C:2]1[C:7]([C:8]([OH:10])=[O:9])=[C:6]([C:12]([F:14])([F:13])[F:15])[CH:5]=[C:4]([CH3:16])[N:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 23092426Methyl 2,6-dimethyl-4-trifluoromethylpyridine-3-carboxylate

Product 1

HCID 671281022,6-Dimethyl-4-trifluoromethylpyridine-3-carboxylic acid hydrochloride

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Methyl 2,6-dimethyl-4-trifluoromethylpyridine-3-carboxylate (23.30 g, 99.9 mmol) was dissolved in ethanol (50 mL). A 5-mol/L aqueous potassium hydroxide solution (50 mL, 250 mmol) was added to the solution, followed by refluxing for 2 days. The reaction mixture was allowed to stand for cooling, and concentrated hydrochloric acid (15 mL) was added to the resultant mixture, followed by concentration under reduced pressure. To the obtained residue, ethanol was added, and the mixture was heated for dissolution. Insoluble matter was removed through filtration, and the filtrate was concentrated under reduced pressure. Ether was added to the thus-obtained residue, and the solid was collected through filtration, to thereby yield 2,6-dimethyl-4-trifluoromethylpyridine-3-carboxylic acid hydrochloride as a colorless powder (25.24 g, 99%).

Workup

  1. temperatureby refluxing for 2 days
  2. temperaturefor cooling
  3. concentrationfollowed by concentration under reduced pressure
  4. additionTo the obtained residue, ethanol was added
  5. temperaturethe mixture was heated for dissolution
  6. customInsoluble matter was removed through filtration
  7. concentrationthe filtrate was concentrated under reduced pressure
  8. additionEther was added to the thus-obtained residue
  9. filtrationthe solid was collected through filtration

Sources & evidence

ORD record
ord-f234da22edcf4253acfa3828534845f7
Source dataset
uspto-grants-2008_12
Patent number
US07459552B2

Reaction notes

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