Hydrochloric Acid → HCID 70663168, compound

HRID 878231Notes

Reaction equation

HRID 878231 reaction equation
Cl[C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([C:11]([F:14])([F:13])[F:12])[N:10]=1)[C:5]([OH:7])=[O:6].[CH3:15][OH:16].C[O-].[Na+].Cl>CCOC(C)=O>[CH3:15][O:16][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([C:11]([F:14])([F:13])[F:12])[N:10]=1)[C:5]([OH:7])=[O:6]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 10942334Sodium MethoxideHCID 112183892-Chloro-6-(trifluoromethyl)pyridine-4-carboxylic acid

Product 1

HCID 70663168HCID 70663168, compoundYield 90.4%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-chloro-6-(trifluoromethyl)isonicotinic acid (0.15 g, 665 μmol, prepared according to F. Cottet, M. Schlosser, Eur. J. Org. Chem. 2004, 18, 3793-3798) in methanol (2 mL) sodium methoxide (79.0 mg, 1.46 mmol) was added and the reaction refluxed for 5 hours. Another 287 mg (5.32 mmol) sodium methoxide was added and the white suspension was stirred at reflux temperature overnight. After 23 hours the suspension was allowed to cool to room temperature and was poured on saturated 1M HCl solution and EtOAc and the layers were separated. The aqueous layer was extracted twice with EtOAc. The organic layers were washed once with brine, dried over MgSO4, filtered and evaporated to give the desired compound as a colorless solid (0.133 g; 90%). MS (ESI): m/z=220.02 [M−H]−.

Workup

  1. temperaturethe reaction refluxed for 5 hours
  2. temperatureat reflux temperature overnight
  3. customthe layers were separated
  4. extractionThe aqueous layer was extracted twice with EtOAc
  5. washThe organic layers were washed once with brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-4c621cb4f9d342bbb64dbda2aa5e085a
Source dataset
uspto-grants-2015_03
Patent number
US08987307B2

Reaction notes

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