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

HRID 382873Notes

Reaction equation

HRID 382873 reaction equation
[Cl: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>O>[Cl: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

5

Reactant 3

HCID 280Carbon DioxideHCID 28175-Chloro-8-hydroxyquinolineHCID 11430Potassium Carbonate

Product 1

HCID 145347675-Chloro-8-hydroxyquinoline-7-carboxylic acidYield 23.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
170 °C

Procedure

5Chloro-8-hydroxyquinoline (5.00 g) and potassium carbonate (11.54 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 dissolved in 800 mL water. The insoluble material is filtered and 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. The resulting solid is collected, washed with water and dried. The crude product is triturated with i-PrOH and dried to yield 1.481 g of the title product as a brown solid.

Workup

  1. temperatureThe reaction is cooled
  2. filtrationThe insoluble material is filtered
  3. custompartitioned between 800 mL water and 400 mL EtOAc in a separatory funnel
  4. washThe aqueous layer is washed with EtOAc (3×400 mL)
  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-57d2179cc7fa480a85492423540ceca8
Source dataset
uspto-grants-2001_10
Patent number
US06310211B1

Reaction notes

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