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Bromotrichloromethane → 5-Hydroxy-2-trifluoromethyl-quinoline-7-carboxylic acid methyl ester

HRID 887732
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 887732
[CH3:1][O:2][C:3]([CH:5]1[CH2:14][C:13]2[N:12]=[C:11]([C:15]([F:18])([F:17])[F:16])[CH:10]=[CH:9][C:8]=2[C:7](=[O:19])[CH2:6]1)=[O:4].BrC(Cl)(Cl)Cl.N12CCCN=C1CCCCC2>C(Cl)Cl.C(OCC)(=O)C>[CH3:1][O:2][C:3]([C:5]1[CH:14]=[C:13]2[C:8]([CH:9]=[CH:10][C:11]([C:15]([F:18])([F:16])[F:17])=[N:12]2)=[C:7]([OH:19])[CH:6]=1)=[O:4]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 6383BromotrichloromethaneHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 578559035-Oxo-2-trifluoromethyl-5,6,7,8-tetrahydro-quinoline-7-carboxylic acid methyl ester

Produkt 1

HCID 1361498195-Hydroxy-2-trifluoromethyl-quinoline-7-carboxylic acid methyl esterAusbeute 95 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344
Dichloromethane
Lösungsmittel
2×
HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A solution of 5-oxo-2-trifluoromethyl-5,6,7,8-tetrahydro-quinoline-7-carboxylic acid methyl ester (50.0 g) is dissolved in methylene chloride (500 mL) and treated drop wise with a solution of bromotrichloromethane (54.43 g) and 1,8-diazabicylo[5.4.0]undec-7-en (55.72 g) in methylene chloride (100 mL) at 0-5° C. After the addition is complete, the reaction mixture is allowed to warm to room temperature, and stirred for 1 h. The reaction mixture is diluted with ethyl acetate and then washed successively with diluted aqueous hydrochloric acid and brine. The ethyl acetate phase is dried over anhydrous sodium sulfate, filtered and concentrated in vacuum. The residue is purified by recrystallization from hexane/ethyl acetate to give 47.13 g of the title compound of the formula

Aufarbeitung

  1. additionAfter the addition
  2. washwashed successively with diluted aqueous hydrochloric acid and brine
  3. dry with materialThe ethyl acetate phase is dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuum
  6. customThe residue is purified by recrystallization from hexane/ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-58360df6e7964d1a86fa984202de6f98
Quelldatensatz
uspto-grants-2012_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08247431B2

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