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

HRID 51916

Reaktionsgleichung

Reaktionsgleichung von HRID 51916
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

Komponenten

4

Edukt 2

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

Produkt 1

HCID 222627192-(4-Trifluoromethylphenyl)nicotinic acidAusbeute 101,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 66577907Tetrahydrofuran-methanol waterLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-5c0e912c0bed4bc0a348eec2ec6c0d3f
Quelldatensatz
uspto-grants-2004_03
Patentnummer
US06713489B2

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