Carbon Dioxide → 8-Hydroxyquinoline-7-carboxylic Acid

HRID 2301406Notes

Reaction equation

HRID 2301406 reaction equation
[OH:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[CH:9][CH:8]=[CH:7]2.[C:12](=O)([O-:14])[O-:13].[K+].[K+].C(=O)=O>>[OH:1][C:2]1[C:3]([C:12]([OH:14])=[O:13])=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[CH:9][CH:8]=[CH:7]2

Participants

4

Reactant 3

HCID 280Carbon DioxideHCID 19238-HydroxyquinolineHCID 11430Potassium Carbonate

Product 1

HCID 2313638-Hydroxyquinoline-7-carboxylic AcidYield 79.8%

Conditions

Temperature
170 °C

Procedure

8-Hydroxyquinoline (50.0 g) and potassium carbonate (142.8 g) are mixed together in a stainless steel bomb and heated at 170° C. under 1200 p.s.i. CO2 for 7 days. The reaction is then cooled and the resulting solid is partitioned between water (6 L) and EtOAc (1 L). The organic layer is extracted with water (2×300 mL). The combined aqueous layers are extracted with EtOAc (3×500 mL). The aqueous layer is then acidified to pH 4.5 with conc. HCl. The resulting solid is collected, dried and triturated with i-PrOH to yield 51.97 g of the title compound as a tan solid.

Workup

  1. temperatureThe reaction is then cooled
  2. customthe resulting solid is partitioned between water (6 L) and EtOAc (1 L)
  3. extractionThe organic layer is extracted with water (2×300 mL)
  4. extractionThe combined aqueous layers are extracted with EtOAc (3×500 mL)
  5. customThe resulting solid is collected
  6. customdried
  7. customtriturated with i-PrOH

Sources & evidence

ORD record
ord-79de921b83dd406fa62ff40b5a445a2b
Source dataset
uspto-grants-2002_12
Patent number
US06500842B1

Reaction notes

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