2,2,2-Trifluoroacetophenone → HCID 178498430, Verbindung

HRID 60128

Reaktionsgleichung

Reaktionsgleichung von HRID 60128
S(Cl)(Cl)=O.[F:5][C:6]([F:16])([F:15])[C:7]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=O.[CH3:17][O:18][C:19]([C:21]1[CH:26]=[CH:25][N:24]=[C:23]([NH2:27])[CH:22]=1)=[O:20].[OH-].[Na+]>N1C=CC=CC=1>[F:5][C:6]([F:16])([F:15])/[C:7](=[N:27]\[C:23]1[CH:22]=[C:21]([CH:26]=[CH:25][N:24]=1)[C:19]([O:18][CH3:17])=[O:20])/[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Komponenten

6

Edukt 4

HCID 99052,2,2-TrifluoroacetophenoneHCID 14798Sodium HydroxideHCID 24386Thionyl ChlorideHCID 236984Methyl 2-aminopyridine-4-carboxylate

Produkt 1

HCID 178498430HCID 178498430, VerbindungAusbeute 27,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Versuchsvorschrift

Thionyl chloride (2.2 ml) was added at 0° C. to a pyridine (4.8 ml) solution of 2,2,2-trifluoro-1-phenylethanone (5.1 g) and 2-aminopyridine-4-carboxylic acid methyl ester (4.5 g). The temperature of the reaction solution was increased to room temperature, and the reaction solution was then stirred for 1 hour. Thereafter, the reaction solution was poured into a 1 N sodium hydroxide aqueous solution, and the mixed solution was then extracted with ethyl acetate. Organic layers were gathered, and the gathered organic layer was then dried over anhydrous sodium sulfate. After that, the solvent was distilled away under reduced pressure. The obtained residue was purified by silica gel column chromatography (silica gel: eluent; heptane:ethyl acetate=2:1-1:1), so as to obtain the title compound (2.5 g) in the form of a yellow liquid.

Aufarbeitung

  1. extractionthe mixed solution was then extracted with ethyl acetate
  2. dry with materialthe gathered organic layer was then dried over anhydrous sodium sulfate
  3. distillationAfter that, the solvent was distilled away under reduced pressure
  4. customThe obtained residue was purified by silica gel column chromatography (silica gel: eluent; heptane:ethyl acetate=2:1-1:1)

Quellen und Nachweise

ORD-Eintrag
ord-7b51dea22de641019236184e5be34a55
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09440970B2

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