Carbon Dioxide → 8-Hydroxy-2-methylquinoline-7-carboxylic acid

HRID 382876

Reaktionsgleichung

Reaktionsgleichung von HRID 382876
[OH:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9]([CH3:12])[CH:8]=[CH:7]2.[C:13](=O)([O-:15])[O-:14].[K+].[K+].C(=O)=O>>[CH3:12][C:9]1[CH:8]=[CH:7][C:6]2[C:11](=[C:2]([OH:1])[C:3]([C:13]([OH:15])=[O:14])=[CH:4][CH:5]=2)[N:10]=1

Komponenten

4

Edukt 3

HCID 280Carbon DioxideHCID 11430Potassium CarbonateHCID 132242-Methyl-8-hydroxyquinoline

Produkt 1

HCID 4698238-Hydroxy-2-methylquinoline-7-carboxylic acidAusbeute 29,1 %

Reaktionsbedingungen

Temperatur
170 °C

Versuchsvorschrift

8-Hydroxyquinaldine (5.0 g) and potassium carbonate (13.02 g) are mixed together in a stainless steel bomb and heated to 170° C. under 800 p.s.i. CO2 for 6 days. The reaction is then cooled and the resulting solid is partitioned between EtOAc and water. The organic layer is extracted with water (3×). The combined aqueous layers are washed with EtOAc (3×). The aqueous layer is then acidified to pH 4.5 with conc. HCl. The resulting solid is collected, dried and recrystallized from i-PrOH to yield 1.86 g of the title compound as a gold solid.

Aufarbeitung

  1. temperatureThe reaction is then cooled
  2. customthe resulting solid is partitioned between EtOAc and water
  3. extractionThe organic layer is extracted with water (3×)
  4. washThe combined aqueous layers are washed with EtOAc (3×)
  5. customThe resulting solid is collected
  6. customdried
  7. customrecrystallized from i-PrOH

Quellen und Nachweise

ORD-Eintrag
ord-e4696e4a1731472a86d86fc9c14596fa
Quelldatensatz
uspto-grants-2001_10
Patentnummer
US06310211B1

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