Methanol → 6-Morpholin-4-yl-4-phenoxy-nicotinic acid

HRID 2186791

Reaktionsgleichung

Reaktionsgleichung von HRID 2186791
C([O:3][C:4](=[O:24])[C:5]1[C:10]([O:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:9][C:8]([N:18]2[CH2:23][CH2:22][O:21][CH2:20][CH2:19]2)=[N:7][CH:6]=1)C.CO.[OH-].[Na+]>O>[N:18]1([C:8]2[CH:9]=[C:10]([O:11][C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=3)[C:5]([C:4]([OH:24])=[O:3])=[CH:6][N:7]=2)[CH2:23][CH2:22][O:21][CH2:20][CH2:19]1

Komponenten

5

Edukt 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 538442216-Morpholin-4-yl-4-phenoxy-nicotinic acid ethyl ester

Produkt 1

HCID 181853776-Morpholin-4-yl-4-phenoxy-nicotinic acidAusbeute 77 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

A mixture of 66 mg (0.20 mmol) 6-morpholin-4-yl-4-phenoxy-nicotinic acid ethyl ester, 2 ml methanol and 2 ml 1N aqueous sodium hydroxide solution was stirred at room temperature for 1 h. The reaction mixture was diluted with water and washed with tert-butyl-methyl-ether. The aqueous layer was acidified to pH 4-5 with concentrated hydrochloric acid solution and extracted with 3 portions of dichloromethane. The combined organic layers were washed with saturated aqueous sodium chloride solution and dried with sodium sulfate. Concentration afforded 46 mg (77%) of the title compound as a white solid.

Aufarbeitung

  1. washwashed with tert-butyl-methyl-ether
  2. extractionextracted with 3 portions of dichloromethane
  3. washThe combined organic layers were washed with saturated aqueous sodium chloride solution
  4. dry with materialdried with sodium sulfate
  5. concentrationConcentration

Quellen und Nachweise

ORD-Eintrag
ord-ac813b30d0844dad8951f09f6a019593
Quelldatensatz
uspto-grants-2002_06
Patentnummer
US06407111B1

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