Carbon Dioxide → 2-Chloroquinoline-8-carboxylic acid

HRID 1055998

Reaktionsgleichung

Reaktionsgleichung von HRID 1055998
[Li]CCCC.Br[C:7]1[CH:8]=[CH:9][CH:10]=[C:11]2[C:16]=1[N:15]=[C:14]([Cl:17])[CH:13]=[CH:12]2.[C:18](=[O:20])=[O:19]>C1COCC1>[Cl:17][C:14]1[CH:13]=[CH:12][C:11]2[C:16](=[C:7]([C:18]([OH:20])=[O:19])[CH:8]=[CH:9][CH:10]=2)[N:15]=1

Komponenten

5

Edukt 3

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

Produkt 1

HCID 190262012-Chloroquinoline-8-carboxylic acidAusbeute 99 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

nBuLi (2.2M in hexanes; 7.50 ml, 16.49 mmol) was added dropwise over 2 min to a solution of 8-bromo-2-chloroquinoline (4.00 g, 16.49 mmol, Biofine International, Inc., Vancouver, BC) in THF (82 ml) at −78° C. The resulting mixture was stirred at −78° C. for 20 min before CO2 was bubbled into the solution for 5 min at −78° C. The mixture was quenched with 2 N HCl (10 ml). The resulting mixture was partitioned between 100 ml of Et2O and 1 N NaOH. The organic layer was separated, and the aq. layer was acidified to ˜pH 2 with 5 N HCl and extracted 3 times with 150 ml Et2O. The combined organic extracts were dried over Na2SO4 and concentrated to provide 2-chloroquinoline-8-carboxylic acid (181a, >99% yield) as a light brown solid. MS (ESI, pos. ion) m/z: 208.2 (M+1).

Aufarbeitung

  1. customwas bubbled into the solution for 5 min at −78° C
  2. customThe mixture was quenched with 2 N HCl (10 ml)
  3. customThe resulting mixture was partitioned between 100 ml of Et2O and 1 N NaOH
  4. customThe organic layer was separated
  5. extractionextracted 3 times with 150 ml Et2O
  6. dry with materialThe combined organic extracts were dried over Na2SO4
  7. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-c713b72df7fa473e8080eb0ea2fd3871
Quelldatensatz
uspto-grants-2016_07
Patentnummer
US09394297B2

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