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

HRID 1517994Notes

Reaction equation

HRID 1517994 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 obtained in Step 4 (6.0 g, 13.0 mmol) was suspended in ethanol (480 ml) and 4N aqueous sodium hydroxide solution (84 ml, 21 mmol) was added. The mixture was heated under reflux for 30 min. After allowing the mixture to cool, the reaction solution was partly concentrated under reduced pressure. Hydrochloric acid was added and the precipitate was collected by filtration, washed with water and ethanol and vacuum-dried to give an 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 solution was partly concentrated under reduced pressure
  5. additionHydrochloric acid was added
  6. filtrationthe precipitate was collected by filtration
  7. washwashed with water and ethanol
  8. customvacuum-dried

Sources & evidence

ORD record
ord-b7da74c7e3fd42758623d1228619b3d0
Source dataset
uspto-grants-2012_07
Patent number
US08232401B2

Reaction notes

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