Potassium Hydroxide → 8-Chloro-4-oxo-1,4-dihydro-2,5-quinolinedicarboxylic acid

HRID 272564Notes

Reaction equation

HRID 272564 reaction equation
C[O:2][C:3]([C:5]1[C:6]2[C:7](=[O:21])[CH:8]=[C:9]([C:16]([O:18]CC)=[O:17])[NH:10][C:11]=2[C:12]([Cl:15])=[CH:13][CH:14]=1)=[O:4].[OH-].[K+]>C(O)C>[Cl:15][C:12]1[C:11]2[NH:10][C:9]([C:16]([OH:18])=[O:17])=[CH:8][C:7](=[O:21])[C:6]=2[C:5]([C:3]([OH:4])=[O:2])=[CH:14][CH:13]=1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 589596858-Chloro-4-oxo-1,4-dihydro-2,5-quinolinedicarboxylic acid 2-ethyl 5-methyl ester

Product 1

HCID 589597088-Chloro-4-oxo-1,4-dihydro-2,5-quinolinedicarboxylic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 24 (10.0 g, 32.3 mmol) in ethanol (100 mL) was added 10% aqueous KOH solution (100 mL) at room temperature. The reaction mixture was heated at 100° C. for 24 h and then cooled to room temperature. The reaction mixture was concentrated in vacuum. The resulting aqueous solution was acidified with 2N HCl to pH=6.5, where a solid precipitated and was collected through a filtration. The solid was washed with H2O (100 mL) and Et2O (100 mL), and dried in vacuum at 60° C. to give an off-white solid (25, 8.00 g, 92.9%). 1H NMR (DMSO-d6, 300 MHz) δ ?7.97 (d, J=7.8 Hz, 1H), 7.39 (d, J=7.8 Hz, 1H), 6.90 (s, 1H).

Workup

  1. temperaturecooled to room temperature
  2. concentrationThe reaction mixture was concentrated in vacuum
  3. customprecipitated
  4. filtrationwas collected through a filtration
  5. washThe solid was washed with H2O (100 mL) and Et2O (100 mL)
  6. customdried in vacuum at 60° C.
  7. customto give an off-white solid (25, 8.00 g, 92.9%)

Sources & evidence

ORD record
ord-450c93e91898418aa46546df0e4e37f8
Source dataset
uspto-grants-2008_11
Patent number
US07456178B2

Reaction notes

Loading…