Carbon Dioxide → 2-Chloroquinoline-8-carboxylic acid

HRID 2359429

Reaktionsgleichung

Reaktionsgleichung von HRID 2359429
Br[C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9]([Cl:12])[CH:8]=[CH:7]2.C([Li])CCC.[C:18](=[O:20])=[O:19].O>C1(C)C=CC=CC=1>[Cl:12][C:9]1[CH:8]=[CH:7][C:6]2[C:11](=[C:2]([C:18]([OH:20])=[O:19])[CH:3]=[CH:4][CH:5]=2)[N:10]=1

Komponenten

6

Edukt 4

HCID 280Carbon DioxideHCID 962WaterHCID 109557558-Bromo-2-chloroquinolineHCID 178418339Butyllithium

Produkt 1

HCID 190262012-Chloroquinoline-8-carboxylic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

To a solution of 8-bromo-2-chloroquinoline (14.3 g, 60 mmol) in toluene (90 mL) at −75° C. was added butyllithium in hexanes (2 mol/L, 30 mL) and the reaction mixture was kept for 20 min at −75° C. The reaction mixture was poured onto an excess of freshly crushed dry ice. Water was added (200 mL), and the aqueous layer was washed with ethyl acetate (3×100 mL), acidified to pH 1 with HCl (aq), and extracted with CH2Cl2 (3×100 mL). The combined organic layers were dried, and concentrated to afford 2-chloroquinoline-8-carboxylic acid as a white solid. Yield 6.56 g (53.6%).

Aufarbeitung

  1. washthe aqueous layer was washed with ethyl acetate (3×100 mL)
  2. extractionextracted with CH2Cl2 (3×100 mL)
  3. customThe combined organic layers were dried
  4. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-087c84dcf3634514b46028dfd98bd20a
Quelldatensatz
uspto-grants-2014_04
Patentnummer
US08685970B2

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