Carbon Dioxide → 5-Fluoro-8-hydroxyquinoline-7-carboxylic acid

HRID 1069514Notes

Reaction equation

HRID 1069514 reaction equation
[F:1][C:2]1[CH:11]=[CH:10][C:9]([OH:12])=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2.[C:13](=O)([O-:15])[O-:14].[K+].[K+].C(=O)=O>>[F:1][C:2]1[CH:11]=[C:10]([C:13]([OH:15])=[O:14])[C:9]([OH:12])=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2

Participants

4

Reactant 3

HCID 280Carbon DioxideHCID 11430Potassium CarbonateHCID 2179075-Fluoro-8-quinolinol

Product 1

HCID 183725645-Fluoro-8-hydroxyquinoline-7-carboxylic acidYield 43.8%

Conditions

Temperature
170 °C

Procedure

5-Fluoro-8-hydroxyquinoline (3.00 g) and potassium carbonate (7.62 g) are mixed together in a stainless steel bomb and heated to 170° C. under 800 p.s.i. CO2 for 7 days. The reaction is cooled and the resulting solid is partitioned between 800 mL water and 400 mL EtOAc in a separatory funnel. The aqueous layer is washed with EtOAc (3×400 mL). The aqueous layer is then acidified to pH 4.5 with conc. HCl and cooled. The resulting solid is collected, washed with water and dried. The crude product is triturated with i-PrOH and dried to yield 1.67 g of the title product as a brown solid.

Workup

  1. temperatureThe reaction is cooled
  2. customthe resulting solid is partitioned between 800 mL water and 400 mL EtOAc in a separatory funnel
  3. washThe aqueous layer is washed with EtOAc (3×400 mL)
  4. temperaturecooled
  5. customThe resulting solid is collected
  6. washwashed with water
  7. customdried
  8. customThe crude product is triturated with i-PrOH
  9. customdried

Sources & evidence

ORD record
ord-af7e72a7aab142d0b900255323fc713a
Source dataset
uspto-grants-2001_06
Patent number
US06252080B1

Reaction notes

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