Hydrochloric Acid → 5-Hydroxy-1,8-naphthyridine-2,6-dicarboxylic acid

HRID 1253517Notes

Reaction equation

HRID 1253517 reaction equation
C([O:3][C:4]([C:6]1[C:7]([OH:19])=[C:8]2[C:13](=[N:14][CH:15]=1)[N:12]=[C:11]([C:16]([OH:18])=[O:17])[CH:10]=[CH:9]2)=[O:5])C.[OH-].[K+].Cl>O>[OH:19][C:7]1[C:6]([C:4]([OH:5])=[O:3])=[CH:15][N:14]=[C:13]2[C:8]=1[CH:9]=[CH:10][C:11]([C:16]([OH:18])=[O:17])=[N:12]2

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 178469691HCID 178469691, compound

Product 1

HCID 1785241395-Hydroxy-1,8-naphthyridine-2,6-dicarboxylic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 6-(ethoxycarbonyl)-5-hydroxy-1,8-naphthyridine-2-carboxylic acid (70 g, 270 mmol) in water (700 mL) was added potassium hydroxide (100 g, 560 mmol). The reaction mixture was heated to reflux. After 2 hours, the reaction mixture was cooled and acidified with hydrochloric acid (5 M) to pH 2.5. The yellow precipitates were filtered and washed with water and pyridine to afford 5-hydroxy-1,8-naphthyridine-2,6-dicarboxylic acid.

Workup

  1. temperatureThe reaction mixture was heated to reflux
  2. temperaturethe reaction mixture was cooled
  3. customThe yellow precipitates
  4. filtrationwere filtered
  5. washwashed with water and pyridine

Sources & evidence

ORD record
ord-d55874af07b145bc906dedd23306d758
Source dataset
uspto-grants-2013_06
Patent number
US08455477B2

Reaction notes

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