Sodium Hydroxide → HCID 178524718, compound

HRID 1168822Notes

Reaction equation

HRID 1168822 reaction equation
[OH:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([C:12]([F:15])([F:14])[F:13])=[CH:9][CH:10]=2)[N:5]=[CH:4][C:3]=1[C:16]([O:18]CC)=[O:17].[OH-].[Na+]>CO>[OH:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([C:12]([F:15])([F:13])[F:14])=[CH:9][CH:10]=2)[N:5]=[CH:4][C:3]=1[C:16]([OH:18])=[O:17]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 178469560HCID 178469560, compound

Product 1

HCID 178524718HCID 178524718, compoundYield 28.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of ethyl 4-hydroxy-7-(trifluoromethyl)-3-quinolinecarboxylate (43.4 g, 0.521 mol) and 10% sodium hydroxide (150 mL) was heated to reflux. Most of the ester did not dissolve so methanol (150 mL) was added over the course of an hour to facilitate dissolution. After refluxing for 2 hours a solution was obtained. The solution was refluxed for an additional 2 hours and then allowed to cool to ambient temperature overnight. The methanol was removed under reduced pressure and the resulting aqueous solution was acidified with concentrated hydrochloric acid. The resulting precipitate was isolated by filtration, washed with water and then dried in a vacuum oven at 120° C. for 24 hours to provide 38.5 g of 4-hydroxy-7-(trifluoromethyl)-3-quinolinecarboxylic acid as a white solid.

Workup

  1. temperaturewas heated to reflux
  2. additionwas added over the course of an hour
  3. dissolutiondissolution
  4. temperatureAfter refluxing for 2 hours a solution
  5. customwas obtained
  6. temperatureThe solution was refluxed for an additional 2 hours
  7. customThe methanol was removed under reduced pressure
  8. customThe resulting precipitate was isolated by filtration
  9. washwashed with water
  10. customdried in a vacuum oven at 120° C. for 24 hours

Sources & evidence

ORD record
ord-99016d50a2c8499c991198fed7d24086
Source dataset
uspto-grants-2003_09
Patent number
US06627640B2

Reaction notes

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