Methanol → methyl 6-(trifluoromethyl)nicotinate

HRID 1620979Notes

Reaction equation

HRID 1620979 reaction equation
[F:1][C:2]([F:13])([F:12])[C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=[O:8])=[CH:5][N:4]=1.OS(O)(=O)=O.[CH3:19]O>>[F:13][C:2]([F:1])([F:12])[C:3]1[CH:11]=[CH:10][C:6]([C:7]([O:9][CH3:19])=[O:8])=[CH:5][N:4]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 27775516-(Trifluoromethyl)nicotinic acid

Product 1

HCID 2775647methyl 6-(trifluoromethyl)nicotinateYield 100%

Procedure

To a solution of 6-(trifluoromethyl)nicotinic acid (3.82 g, 20 mmol) in 120 mL of methanol was added 5 mL of concentrated H2SO4 and the mixture was refluxed for 5 hours. Most of the solvent was removed in vacuo and the pH of the residue was adjusted to about 7 by 1N HCl. The mixture was extracted with ethyl acetate (100 mL×3), and the combined organic layers were dried over Na2SO4, filtered, and concentrated in vacuo to provide the title compound (4.1 g, 100%).

Workup

  1. temperaturethe mixture was refluxed for 5 hours
  2. customMost of the solvent was removed in vacuo
  3. extractionThe mixture was extracted with ethyl acetate (100 mL×3)
  4. dry with materialthe combined organic layers were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-17872d51c2994f6ba7bea11c4e06ad86
Source dataset
uspto-grants-2014_07
Patent number
US08772500B2

Reaction notes

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