Lithium hydroxide, monohydrate → 2-(4-Trifluoromethylphenyl)nicotinic acid

HRID 841779Notes

Reaction equation

HRID 841779 reaction equation
C([O:3][C:4](=[O:21])[C:5]1[CH:10]=[CH:9][CH:8]=[N:7][C:6]=1[C:11]1[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][CH:12]=1)C.O.[OH-].[Li+]>O1CCCC1CO.O>[F:19][C:17]([F:18])([F:20])[C:14]1[CH:13]=[CH:12][C:11]([C:6]2[N:7]=[CH:8][CH:9]=[CH:10][C:5]=2[C:4]([OH:21])=[O:3])=[CH:16][CH:15]=1

Participants

4

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 579874152-(4-Trifluoromethyl-phenyl)-nicotinic acid ethyl ester

Product 1

HCID 222627192-(4-Trifluoromethylphenyl)nicotinic acidYield 101.9%

Reagents, catalysts & solvents 1

HCID 66577907Tetrahydrofuran-methanol waterSolvent

Procedure

2-(4-Trifluoromethyl-phenyl)-nicotinic acid ethyl ester (2.33 g, 7.9 mmol) was dissolved in 40 ml of a 3:1:1 mixture of tetrahydrofuran-methanol-water, and lithium hydroxide monohydrate (828 mg, 19.8 mmol) was added. After stirring overnight at room temperature, the volatiles were removed under vacuum and 75 ml of water was added to the mixture, which was brought to pH 2 with 1N HCl. The resulting slurry was extracted with 2×100 ml of ethyl acetate, the combined organic layers were washed with brine, dried (magnesium sulfate), filtered and concentrated under vacuum to provide 2.15 g of the title compound as a colorless solid.

Workup

  1. additionwas added
  2. customthe volatiles were removed under vacuum and 75 ml of water
  3. additionwas added to the mixture, which
  4. extractionThe resulting slurry was extracted with 2×100 ml of ethyl acetate
  5. washthe combined organic layers were washed with brine
  6. dry with materialdried (magnesium sulfate)
  7. filtrationfiltered
  8. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-90180f7e02bf4828ac4eebf952995be2
Source dataset
uspto-grants-2002_04
Patent number
US06369075B1

Reaction notes

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