Methanol → 4-(4-Chloro-2-fluorophenyl)nicotinic acid

HRID 1398288Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1398288
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:13]([C:14]([O:16]C)=[O:15])=[CH:12][N:11]=[CH:10][CH:9]=2)=[C:4]([F:18])[CH:3]=1.CO.[OH-].[Na+]>O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:13]([C:14]([OH:16])=[O:15])=[CH:12][N:11]=[CH:10][CH:9]=2)=[C:4]([F:18])[CH:3]=1

Komponenten

5

Edukt 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 86695906Methyl 4-(4-chloro-2-fluorophenyl)nicotinate

Produkt 1

HCID 866959074-(4-Chloro-2-fluorophenyl)nicotinic acidAusbeute 63,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a solution of methyl 4-(4-chloro-2-fluorophenyl)nicotinate (15 g, 56.5 mmol) (as prepared in Ex 1, Part B) in a solvent mixture of methanol (150 mL) and water (150 mL) cooled to 0° C. was added sodium hydroxide (9.03 g, 226 mmol) and the mixture was warmed to room temperature and stirred for 1 h. The reaction mixture was concentrated under reduced pressure and pH of the resultant aqueous solution was adjusted to pH=4 using 1.5 N Hydrochloric acid during which time the product crashed out as a solid. Filtration of the mixture provided 4-(4-chloro-2-fluorophenyl)nicotinic acid (9 g, 35.8 mmol, 63% yield) as an off white solid. LC/MS (ESI) m/e 252.0 [(M+H)+, calcd for C12H8ClFNO2 252.1]; LC/MS retention time (method A): tR=0.97 min.

Aufarbeitung

  1. temperaturethe mixture was warmed to room temperature
  2. concentrationThe reaction mixture was concentrated under reduced pressure and pH of the resultant aqueous solution
  3. filtrationFiltration of the mixture

Quellen und Nachweise

ORD-Eintrag
ord-1a5a406f56ef4ec79cd4bbe4d4117485
Quelldatensatz
uspto-grants-2014_12
Patentnummer
US08901305B2

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