Sodium Hydroxide → 6-(5-Methyl-3-phenyl-isoxazol-4-ylmethoxy)-nicotinic acid

HRID 83119

Reaktionsgleichung

Reaktionsgleichung von HRID 83119
C[O:2][C:3](=[O:24])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:11][C:12]2[C:13]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[N:14][O:15][C:16]=2[CH3:17])=[N:6][CH:5]=1.[OH-].[Na+]>C(O)C>[CH3:17][C:16]1[O:15][N:14]=[C:13]([C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[C:12]=1[CH2:11][O:10][C:7]1[CH:8]=[CH:9][C:4]([C:3]([OH:24])=[O:2])=[CH:5][N:6]=1

Komponenten

4

Edukt 2

HCID 14798Sodium HydroxideHCID 665992926-(5-Methyl-3-phenyl-isoxazol-4-ylmethoxy)-nicotinic acid methyl ester

Produkt 1

HCID 665992136-(5-Methyl-3-phenyl-isoxazol-4-ylmethoxy)-nicotinic acidAusbeute 45 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

To a solution of 6-(5-methyl-3-phenyl-isoxazol-4-ylmethoxy)-nicotinic acid methyl ester (3.89 g, 120 mmol) in ethanol (40 mL) was added aqueous sodium hydroxide (1 M, 36.0 mL, 36.0 mmol). After heating at reflux for 2 h it was cooled to ambient temperature and concentrated. Addition of aqueous sodium hydroxide (1 M, 50 mL) was followed by washing with tert-butylmethylether (100 mL). The aqueous phase was acidified with aqueous hydrogen chloride (conc.) to pH=1 and extracted with tert-butylmethylether (100 mL). The organic layer was washed with water (50 mL) and aqueous sodium chloride (saturated, 50 mL). Drying over sodium sulfate and concentration afforded the title compound (1.68 g, 45%) as an off white solid. MS: m/e=309.3 [M−H]−.

Aufarbeitung

  1. temperatureAfter heating
  2. temperatureat reflux for 2 h it
  3. concentrationconcentrated
  4. additionAddition of aqueous sodium hydroxide (1 M, 50 mL)
  5. washby washing with tert-butylmethylether (100 mL)
  6. extractionextracted with tert-butylmethylether (100 mL)
  7. washThe organic layer was washed with water (50 mL) and aqueous sodium chloride (saturated, 50 mL)
  8. dry with materialDrying over sodium sulfate and concentration

Quellen und Nachweise

ORD-Eintrag
ord-398b33738a284c0eac900989499c5c55
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08846719B2

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