Sodium Hydroxide → Quinaldic Acid

HRID 1032737Notes

Reaction equation

HRID 1032737 reaction equation
Br[C:2]1[CH:11]=[C:10]2[C:5]([C:6](=O)[CH:7]=[C:8]([C:19]([O:21]CC)=[O:20])[N:9]2C2C=CC(F)=CC=2)=[CH:4][CH:3]=1.[OH-].[Na+]>C1COCC1>[N:9]1[C:10]2[C:5](=[CH:4][CH:3]=[CH:2][CH:11]=2)[CH:6]=[CH:7][C:8]=1[C:19]([OH:21])=[O:20]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 22164817HCID 22164817, compound

Product 1

HCID 7124Quinaldic AcidYield 203.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
2.5 °C

Procedure

A solution of ethyl 7-bromo-1-(4-fluorophenyl)1,4-dihydro-4-oxoquinolinecarboxylate (100 g; 0.256 mole), 400 ml of lN NaOH and 700 ml of THF was refluxed for 2.5 hrs. It was cooled, THF was removed by distillation and the residue cooled to 0-5° C. It was acidified with 2N HCl, the white solid filtered and washed with 1.5 L. of water The product was dried in an oven at 70° C. for 18 hrs. to give 90.4 g (97.5%) of quinolinecarboxylic acid. This product was used in the next step without further purification.

Workup

  1. temperatureIt was cooled
  2. customTHF was removed by distillation
  3. filtrationthe white solid filtered
  4. washwashed with 1.5 L
  5. dry with materialof water The product was dried in an oven at 70° C. for 18 hrs

Sources & evidence

ORD record
ord-eab02a64a1484af6b7bbba70ff0b4c94
Source dataset
uspto-grants-1990_09
Patent number
US04959363

Reaction notes

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