Citric Acid → 5-(4-Chloro-phenyl)-6-(1-methyl-1H-imidazol-2-ylmethoxy)-nicotinic acid

HRID 1766534Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1766534
C[O:2][C:3](=[O:25])[C:4]1[CH:9]=[C:8]([C:10]2[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][CH:11]=2)[C:7]([O:17][CH2:18][C:19]2[N:20]([CH3:24])[CH:21]=[CH:22][N:23]=2)=[N:6][CH:5]=1.O.[OH-].[Li+].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>O1CCCC1>[Cl:16][C:13]1[CH:14]=[CH:15][C:10]([C:8]2[C:7]([O:17][CH2:18][C:19]3[N:20]([CH3:24])[CH:21]=[CH:22][N:23]=3)=[N:6][CH:5]=[C:4]([CH:9]=2)[C:3]([OH:25])=[O:2])=[CH:11][CH:12]=1

Komponenten

6

Edukt 4

HCID 311Citric AcidHCID 962WaterHCID 3939Lithium HydroxideHCID 675050775-(4-Chloro-phenyl)-6-(1-methyl-1H-imidazol-2-ylmethoxy)-nicotinic acid methyl ester

Produkt 1

HCID 675046735-(4-Chloro-phenyl)-6-(1-methyl-1H-imidazol-2-ylmethoxy)-nicotinic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

5-(4-Chloro-phenyl)-6-(1-methyl-1H-imidazol-2-ylmethoxy)-nicotinic acid methyl ester (0.28 g, 0.8 mmol) was dissolved in tetrahydrofuran (4.5 mL). Water (1.5 mL) and lithium hydroxide (99 mg, 2.3 mmol) was added and the mixture was stirred for 1 h at 80° C. The mixture was cooled to room temperature; citric acid (4 mL, 10%) was added and the mixture was extracted with ethyl acetate. Organic phases were pooled dried with Na2SO4 and the solvent evaporated to give a quantitative yield of the title compound as beige solid, MS (ISP) 342.0 (M−H)−.

Aufarbeitung

  1. temperatureThe mixture was cooled to room temperature
  2. extractionthe mixture was extracted with ethyl acetate
  3. dry with materialOrganic phases were pooled dried with Na2SO4
  4. customthe solvent evaporated

Quellen und Nachweise

ORD-Eintrag
ord-fa4ae61cb9c14f8591871309f2616f16
Quelldatensatz
uspto-grants-2007_06
Patentnummer
US07229999B2

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