Lithium Hydroxide → 2-Methoxy-4-methyl-6-(3-trifluoromethyl-phenyl)-nicotinic acid

HRID 1517067Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1517067
C[O:2][C:3](=[O:23])[C:4]1[C:9]([CH3:10])=[CH:8][C:7]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([C:17]([F:20])([F:19])[F:18])[CH:12]=2)=[N:6][C:5]=1[O:21][CH3:22].[OH-].[Li+].Cl.O>C1COCC1.CO>[CH3:22][O:21][C:5]1[N:6]=[C:7]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([C:17]([F:20])([F:18])[F:19])[CH:12]=2)[CH:8]=[C:9]([CH3:10])[C:4]=1[C:3]([OH:23])=[O:2]

Komponenten

5

Edukt 3

HCID 3939Lithium HydroxideHCID 21885828Hydrate;hydrochlorideHCID 57441128HCID 57441128, Verbindung2×

Produkt 1

HCID 574411372-Methoxy-4-methyl-6-(3-trifluoromethyl-phenyl)-nicotinic acidAusbeute 77,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 21899815MeOH tetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 0.325 g (1.00 mmol) of 2-methoxy-4-methyl-6-(3-trifluoromethyl-phenyl)-nicotinic acid methyl ester (intermediate 5C) in 20 ml of THF/MeOH (1:1) was added 2.50 ml (2.50 mmol) of lithium hydroxide solution (1 molar in water) drop by drop and the reaction mixture was then heated up to reflux. After 8 hours, it was poured into crashed ice and acidified with HCl/H2O (1N) to pH 3.0 and then extracted twice with EtOAc; the organic phases were washed with water, dried over magnesium sulfate, filtered and evaporated. The residue was purified by flash column chromatography (CH2Cl2/MeOH 1:0 to 4:1) to give 0.24 g (77%) of the title compound as light yellow solid. MS: 310.0 (M−H−).

Aufarbeitung

  1. temperaturethe reaction mixture was then heated up
  2. temperatureto reflux
  3. additionit was poured
  4. extractionextracted twice with EtOAc
  5. washthe organic phases were washed with water
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. customevaporated
  9. customThe residue was purified by flash column chromatography (CH2Cl2/MeOH 1:0 to 4:1)

Quellen und Nachweise

ORD-Eintrag
ord-2c73d2bf00ce45a3b63a7792bae5cf7b
Quelldatensatz
uspto-grants-2012_07
Patentnummer
US08227613B2

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