Carbon Dioxide → 8-Hydroxyquinoline-7-carboxylic Acid

HRID 1490034Notes

Reaction equation

HRID 1490034 reaction equation
[K].[OH:2][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:12]=1[N:11]=[CH:10][CH:9]=[CH:8]2.CN(C=O)C.[C:18](=[O:20])=[O:19]>O>[C:18]([C:4]1[C:3]([OH:2])=[C:12]2[C:7]([CH:8]=[CH:9][CH:10]=[N:11]2)=[CH:6][CH:5]=1)([OH:20])=[O:19]

Participants

6

Reactant 4

HCID 280Carbon DioxideHCID 19238-HydroxyquinolineHCID 6228DimethylformamideHCID 5462222Potassium

Product 1

HCID 2313638-Hydroxyquinoline-7-carboxylic AcidYield 30.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Potassium salt of 8-hydroxyquinoline (25 mmol, 4.58 g), DMF (50 mL) and an excess of dry ice were heated in a pressure reactor at 120° C. for 12 hours. After cooling, water (150 mL) was added to the reaction mixture. The insoluble material was filtered off, and the filtrate was evaporated under reduced pressure. To the residue, water was added again, and additional insoluble material was collected by filtration. The filtrate was acidified to pH 4 with concentrated hydrochloric acid. The precipitate was filtered off, washed with water and dried to give 7-carboxy-8-hydroxyquinoline in 30.4% yield (1.44 g).

Workup

  1. temperatureAfter cooling
  2. filtrationThe insoluble material was filtered off
  3. customthe filtrate was evaporated under reduced pressure
  4. additionTo the residue, water was added again
  5. filtrationadditional insoluble material was collected by filtration
  6. filtrationThe precipitate was filtered off
  7. washwashed with water
  8. customdried

Sources & evidence

ORD record
ord-6a18d965dee740b493468164419d57e2
Source dataset
uspto-grants-1997_10
Patent number
US05681832

Reaction notes

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