Methanol → Methyl quinoline-6-carboxylate

HRID 449244Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 449244
[N:1]1[C:10]2[C:5](=[CH:6][C:7]([C:11]([OH:13])=[O:12])=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.S(Cl)(Cl)=O.[CH3:18]O>>[N:1]1[C:10]2[C:5](=[CH:6][C:7]([C:11]([O:13][CH3:18])=[O:12])=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1

Komponenten

4

Edukt 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 825716-Quinolinecarboxylic acid

Produkt 1

HCID 736812Methyl quinoline-6-carboxylateAusbeute 75 %

Reaktionsbedingungen

Temperatur
65 °C

Versuchsvorschrift

To a solution of quinoline-6-carboxylic acid (183 g, 1.06 mol) in methanol (1 lit.), thionyl chloride (150.7 g, 1.2 mol) was added dropwise at 0° C. and then stirred at 65° C. for 12 h. The reaction mixture was concentrated and to the residue dichloromethane and aqueous sodium carbonate solutions were added. The organic layer was dried with sodium sulphate and concentrated to afford the title compound as a brown solid (150 g, 75%).

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated and to the residue dichloromethane and aqueous sodium carbonate solutions
  2. additionwere added
  3. dry with materialThe organic layer was dried with sodium sulphate
  4. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-ec3613bb85b24e36809e4d5e4b97f0b8
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08481739B2

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