Ammonium formate → Methyl 3-(trifluoromethyl)pyridine-4-carboxylate

HRID 389100Notes

Reaction equation

HRID 389100 reaction equation
[CH:1]([O-])=O.[NH4+].Cl[C:6]1[CH:7]=[C:8]([C:12]([C:15]([F:18])([F:17])[F:16])=[CH:13][N:14]=1)[C:9]([OH:11])=[O:10]>CO.[C].[Pd]>[F:16][C:15]([F:18])([F:17])[C:12]1[CH:13]=[N:14][CH:6]=[CH:7][C:8]=1[C:9]([O:11][CH3:1])=[O:10]

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 112646082-Chloro-5-(trifluoromethyl)pyridine-4-carboxylic acid

Product 1

HCID 46311187Methyl 3-(trifluoromethyl)pyridine-4-carboxylateYield 49%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

Ammonium formate (500 mg) and 10% palladium carbon (270 mg) were added to a solution of 2-chloro-5-(trifluoromethyl)isonicotinic acid (1.04 g) in methanol (10 ml), followed by stirring at room temperature for 13 hours. An insoluble substance was removed by celite filtration and the filtrate was concentrated. Thionyl chloride (5 ml) was added to a solution of the resulting residue in methanol (30 ml), followed by heating to reflux for 15 hours. The reaction solution was concentrated, an aqueous saturated sodium hydrogen carbonate solution was added thereto, followed by extraction with ethyl acetate, the organic layer was washed with saturated brine and then dried over anhydrous magnesium sulfate, and the solvent was evaporated to obtain methyl 3-(trifluoromethyl)isonicotinate (463 mg) as an orange solid.

Workup

  1. customAn insoluble substance was removed by celite filtration
  2. concentrationthe filtrate was concentrated
  3. additionThionyl chloride (5 ml) was added to a solution of the resulting residue in methanol (30 ml)
  4. temperatureby heating
  5. temperatureto reflux for 15 hours
  6. concentrationThe reaction solution was concentrated
  7. additionan aqueous saturated sodium hydrogen carbonate solution was added
  8. extractionfollowed by extraction with ethyl acetate
  9. washthe organic layer was washed with saturated brine
  10. dry with materialdried over anhydrous magnesium sulfate
  11. customthe solvent was evaporated

Sources & evidence

ORD record
ord-6a551043312e430688911bf262cabd33
Source dataset
uspto-grants-2013_02
Patent number
US08377923B2

Reaction notes

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