Sodium Hydroxide → 6-[(2,3-Dichlorophenyl)methyl]-1-(2-hydroxyethyl)-4-oxo-quinoline-3-carboxylic acid

HRID 491518Notes

Reaction equation

HRID 491518 reaction equation
C([O:4][CH2:5][CH2:6][N:7]1[C:16]2[C:11](=[CH:12][C:13]([CH2:17][C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([Cl:24])[C:19]=3[Cl:25])=[CH:14][CH:15]=2)[C:10](=[O:26])[C:9]([C:27]([O:29]CC)=[O:28])=[CH:8]1)(=O)C.[OH-].[Na+]>C(O)C>[Cl:25][C:19]1[C:20]([Cl:24])=[CH:21][CH:22]=[CH:23][C:18]=1[CH2:17][C:13]1[CH:12]=[C:11]2[C:16](=[CH:15][CH:14]=1)[N:7]([CH2:6][CH2:5][OH:4])[CH:8]=[C:9]([C:27]([OH:29])=[O:28])[C:10]2=[O:26]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 23083945Ethyl 1-(2-acetoxyethyl)-6-(2,3-dichlorobenzyl)-1,4-dihydro-4-oxo-3-quinolinecarboxylate

Product 1

HCID 52769686-[(2,3-Dichlorophenyl)methyl]-1-(2-hydroxyethyl)-4-oxo-quinoline-3-carboxylic acidYield 88.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Ethyl 1-(2-acetoxyethyl)-6-(2,3-dichlorobenzyl)-1,4-dihydro-4-oxo-3-quinolinecarboxylate (6.0 g, 13.0 mmol) obtained in Step 4 was suspended in ethanol (480 ml), 4N aqueous sodium hydroxide solution (84 ml, 21 mmol) was added, and the mixture was heated under reflux for 30 min. After allowing to cool, the reaction mixture was partially concentrated under reduced pressure and hydrochloric acid was added. The precipitated solid was collected by filtration, washed with water and ethanol, and vacuum dried to give the object product (4.5 g, yield 85%) as a white solid.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 30 min
  3. temperatureto cool
  4. concentrationthe reaction mixture was partially concentrated under reduced pressure and hydrochloric acid
  5. additionwas added
  6. filtrationThe precipitated solid was collected by filtration
  7. washwashed with water and ethanol, and vacuum
  8. customdried

Sources & evidence

ORD record
ord-0fcba17e5d4f41b1b80bdb58b5e177d3
Source dataset
uspto-grants-2009_05
Patent number
US07531554B2

Reaction notes

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