Triethylamine → HCID 178470056, Verbindung

HRID 2093719Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2093719
CCN(CC)CC.[NH2:8][C:9]1[CH:14]=[C:13]([C:15]([F:18])([F:17])[F:16])[CH:12]=[CH:11][C:10]=1[C:19](=O)[CH3:20].[CH2:22]([O:24][C:25](=[O:30])[CH2:26][C:27](Cl)=[O:28])[CH3:23].CCOC(C)=O.CCCCCC>C(Cl)Cl.O>[CH2:22]([O:24][C:25]([C:26]1[C:27]([OH:28])=[N:8][C:9]2[C:10]([C:19]=1[CH3:20])=[CH:11][CH:12]=[C:13]([C:15]([F:18])([F:17])[F:16])[CH:14]=2)=[O:30])[CH3:23]

Komponenten

7

Edukt 4

HCID 8471TriethylamineHCID 118931Ethyl 3-chloro-3-oxopropionateHCID 21226206Ethyl acetate hexaneHCID 468355001-(2-Amino-4-(trifluoromethyl)phenyl)ethan-1-one

Produkt 1

HCID 178470056HCID 178470056, VerbindungAusbeute 87,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

12.6 ml (0.09 mol) NEt3 was added to a solution of 16.6 g (0.08 mol) 1-(2-amino-4-(trifluoromethyl)phenyl)ethanone in DCM (170 ml) and cooled to 0° C. 13.4 ml (0.11 mol) 3-chloro-3-oxo-propanoic acid ethyl ester was subsequently added in drops and the mixture was then stirred for 16 h at RT. The mixture was then diluted with water and extracted with DCM (3×). The combined organic phases were dried over Na2SO4 and concentrated in a vacuum. After CC (EtOAc/hexane 2:3) of the residue, 18.1 g (0.07 mol, 87%) 2-hydroxy-4-methyl-7-(trifluoromethyl)quinoline-3-carboxylic acid ethyl ester was obtained.

Aufarbeitung

  1. extractionextracted with DCM (3×)
  2. dry with materialThe combined organic phases were dried over Na2SO4
  3. concentrationconcentrated in a vacuum

Quellen und Nachweise

ORD-Eintrag
ord-8cb1cb5414104e9d8db05bfdb4ed0de6
Quelldatensatz
uspto-grants-2013_05
Patentnummer
US08445512B2

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