Hydrochloric Acid → 4-Bromoquinoline-6-carboxylic acid

HRID 1072878Notes

Reaction equation

HRID 1072878 reaction equation
[Br:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:12]([O:14]C)=[O:13])[CH:10]=2)[N:5]=[CH:4][CH:3]=1.[OH-].[Na+].Cl>CO.O1CCCC1>[Br:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:12]([OH:14])=[O:13])[CH:10]=2)[N:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium Hydroxide2×HCID 16112718Methyl 4-bromoquinoline-6-carboxylate

Product 1

HCID 223880974-Bromoquinoline-6-carboxylic acidYield 81.8%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Methyl 4-bromo-6-quinolinecarboxylate (6.00 g) was dissolved in methanol (60 ml) and tetrahydrofuran (40 ml). A 1N aqueous sodium hydroxide solution (30 ml) was added to the solution while stirring at room temperature and the mixture was stirred at room temperature for 3 hr. A1N aqueous sodium hydroxide solution (20 ml) was added and the mixture was heated under reflux for 2 hr. The reaction mixture was adjusted to pH 4 with 1N hydrochloric acid. The resulting solid was collected by filtration and washed with water and ether to give 4-bromo-6-quinolinecarboxylic acid (4.65 g) as a white powder.

Workup

  1. stirringthe mixture was stirred at room temperature for 3 hr
  2. temperaturethe mixture was heated
  3. temperatureunder reflux for 2 hr
  4. filtrationThe resulting solid was collected by filtration
  5. washwashed with water and ether

Sources & evidence

ORD record
ord-c7953a1bda064aac9051f6d5d83c7989
Source dataset
uspto-grants-2005_06
Patent number
US06911469B2

Reaction notes

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