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

HRID 638968Notes

Reaction equation

HRID 638968 reaction equation
[Br:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[CH:4][C:3]=1[C:14]([O:16]CC)=[O:15].[OH-].[Na+].Cl>C1COCC1>[Br:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[CH:4][C:3]=1[C:14]([OH:16])=[O:15]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 49758155Ethyl 4-bromo-6-methoxyquinoline-3-carboxylate

Product 1

HCID 684531854-Bromo-6-methoxyquinoline-3-carboxylic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of the ethyl 4-bromo-6-(methyloxy)-3-quinolinecarboxylate (12 g, 38.7 mmol) in THF (120 mL) was added 2N NaOH (45 mL, 90 mmol) dropwise over 15 min. The reaction solution was stirred for 24 h and then neutralized with 2N HCl (pH 6). The THF was removed in vacuo and the resulting aqueous solution was acidified to pH 2. The product was collected by filtration and washed with water and fully dried under vacuum (48 h). Isolated 10.8 g (100%).

Workup

  1. customThe THF was removed in vacuo
  2. filtrationThe product was collected by filtration
  3. washwashed with water
  4. customfully dried under vacuum (48 h)
  5. customIsolated 10.8 g (100%)

Sources & evidence

ORD record
ord-fd7ccc8ad6a247368853a454134c76ac
Source dataset
uspto-grants-2010_04
Patent number
US07691850B2

Reaction notes

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