Hydrochloric Acid → 6-Iodo-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

HRID 230837Notes

Reaction equation

HRID 230837 reaction equation
[OH-].[Na+].C(O)C.[I:6][C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][CH:16]=1)[NH:13][CH:12]=[C:11]([C:17]([O:19]CC)=[O:18])[C:10]2=[O:22].Cl>O>[I:6][C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][CH:16]=1)[NH:13][CH:12]=[C:11]([C:17]([OH:19])=[O:18])[C:10]2=[O:22]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 14798Sodium HydroxideHCID 719682Ethyl 6-iodo-4-oxo-1,4-dihydro-3-quinolinecarboxylate

Product 1

HCID 7196836-Iodo-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Sodium hydroxide (9.8 g) was dissolved in water (61 ml) and ethanol (30 ml) was added. The resultant solution was added to Intermediate 11, and the mixture was heated under reflux for 60 min with stirring under nitrogen. Concentrated hydrochloric acid was added, giving a white precipitate. After stirring for 16 h, the precipitate was filtered off, washed with water and dried in vacuo to give the title compound as a white solid (8.15 g).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 60 min
  3. customgiving a white precipitate
  4. stirringAfter stirring for 16 h
  5. filtrationthe precipitate was filtered off
  6. washwashed with water
  7. customdried in vacuo

Sources & evidence

ORD record
ord-9c3b3b54a267440889128149245793bc
Source dataset
uspto-grants-2009_07
Patent number
US07566786B2

Reaction notes

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