Hydrochloric Acid → 6-Bromo-4-hydroxyquinoline-3-carboxylic acid

HRID 1486924Notes

Reaction equation

HRID 1486924 reaction equation
[OH-].[Na+].[Br:3][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[NH:10][CH:9]=[C:8]([C:14]([O:16]CC)=[O:15])[C:7]2=[O:19].O.Cl>CCO>[Br:3][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[NH:10][CH:9]=[C:8]([C:14]([OH:16])=[O:15])[C:7]2=[O:19]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 689824Ethyl 6-bromo-4-oxo-1,4-dihydroquinoline-3-carboxylate

Product 1

HCID 6932036-Bromo-4-hydroxyquinoline-3-carboxylic acidYield 96%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
75 °C

Procedure

2N Sodium hydroxide (506 mL, 1011.43 mmol) was added to a stirred suspension of ethyl 6-bromo-4-oxo-1H-quinoline-3-carboxylate (59.9 g, 202.29 mmol) in EtOH (590 mL) and the resulting solution stirred at 75° C. for 1.5 h. Water was added and the mixture cooled to 0° C. The pH of the solution was adjusted to 3 using hydrochloric acid and the precipitate collected by filtration. The solid was washed with water, EtOH/water (1:1) then Et2O before being dried to afford the desired material (51.9 g, 96%) as a beige solid. NMR Spectrum: 1H NMR (500 MHz, DMSO-d6) δ 7.80 (1H, d), 8.05 (1H, d), 8.37 (1H, s), 8.93 (1H, s). Mass Spectrum: m/z (ES+)[M+H]+=270.

Workup

  1. temperaturethe mixture cooled to 0° C
  2. filtrationthe precipitate collected by filtration
  3. washThe solid was washed with water, EtOH/water (1:1)
  4. dry with materialEt2O before being dried

Sources & evidence

ORD record
ord-536a122401e9426489b5b677dc4e9482
Source dataset
uspto-grants-2016_08
Patent number
US09428503B2

Reaction notes

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