HCID 178469501, compound → HCID 178524706, compound

HRID 852982Notes

Reaction equation

HRID 852982 reaction equation
C([O:3][C:4]([C:6]1[CH:7]=[N:8][C:9]2[C:14]([C:15]=1[OH:16])=[CH:13][C:12]([Br:17])=[CH:11][CH:10]=2)=[O:5])C>[OH-].[K+].O>[Br:17][C:12]1[CH:13]=[C:14]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][C:6]([C:4]([OH:5])=[O:3])=[C:15]2[OH:16]

Participants

4

Reactant 1

HCID 178469501HCID 178469501, compound

Product 1

HCID 178524706HCID 178524706, compoundYield 100.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 14797Potassium HydroxideSolvent

Procedure

A suspension of 6-bromo-4-hydroxy-quinoline-3-carboxylic acid ethyl ester (102.59 g, 337.7 mmol) in 10% potassium hydroxide in water (689 mL) was heated to reflux for 5 h to afford a light brown solution. After cooling to room temperature, the undissolved solid particles were removed by filtration and the filtrate was extracted with dichloromethane to remove any neutral impurities. The aqueous layer was neutralized with 3.0N hydrochloric acid to afford a white precipitate. Then, the solids were collected by filtration and washed with water. After drying in air, 91 g (98% yield) of 6-bromo-4-hydroxy-quinoline-3-carboxylic acid was isolated as a white solid: EI-HRMS m/e calcd for C10H6BrNO3 (M+) 266.9531, found 266.9521.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 5 h
  3. customto afford a light brown solution
  4. customthe undissolved solid particles were removed by filtration
  5. extractionthe filtrate was extracted with dichloromethane
  6. customto remove any neutral impurities
  7. customto afford a white precipitate
  8. filtrationThen, the solids were collected by filtration
  9. washwashed with water
  10. customAfter drying in air

Sources & evidence

ORD record
ord-57c0c285785e4714a7a6c036720340b8
Source dataset
uspto-grants-2007_08
Patent number
US07253285B2

Reaction notes

Loading…