Hydrochloric Acid → 6-Hydroxyquinoline-2-carboxylic acid

HRID 493423Notes

Reaction equation

HRID 493423 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]=[C:8]([C:13]([OH:15])=[O:14])[CH:7]=[CH:6]2.[OH-].[NH4+].Cl>Br.O>[OH:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]=[C:8]([C:13]([OH:15])=[O:14])[CH:7]=[CH:6]2

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14923Ammonium HydroxideHCID 111832986-methoxyquinoline-2-carboxylic Acid

Product 1

HCID 133367806-Hydroxyquinoline-2-carboxylic acid

Reagents, catalysts & solvents 2

HCID 260Hydrogen BromideSolventHCID 962WaterSolvent

Conditions

Temperature
125 °C

Procedure

6-Methoxy-quinoline-2-carboxylic acid (4 g, 0.019 mol) was suspended in hydrobromic acid 48% in water (80 ml) and the mixture was heated at 125° C. overnight. After cooling to 0° C. ammonium hydroxide was added until the pH was 6-7 followed by addition of HCl until the pH was 3-4 and the compound precipitated. The solid was filtrated, washed with water and dried under vacuum to yield 3.5 g (0.0185 mol, 97% of theory) of the title compound as a yellow solid MS (m/e)=190.1 (M+H)+.

Workup

  1. additionwas added until the pH was 6-7
  2. customthe compound precipitated
  3. filtrationThe solid was filtrated
  4. washwashed with water
  5. customdried under vacuum

Sources & evidence

ORD record
ord-9c87f3eaade24b8497bce2b060f9057e
Source dataset
uspto-grants-2009_05
Patent number
US07534891B2

Reaction notes

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