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

HRID 915787Notes

Reaction equation

HRID 915787 reaction equation
Cl[C:2]1[C:11]2[NH:10][C:9]([C:12]([OH:14])=[O:13])=[CH:8][C:7](=[O:15])[C:6]=2[C:5]([C:16]([OH:18])=[O:17])=[CH:4][CH:3]=1>[OH-].[K+].[Pd]>[O:15]=[C:7]1[C:6]2[C:5]([C:16]([OH:18])=[O:17])=[CH:4][CH:3]=[CH:2][C:11]=2[NH:10][C:9]([C:12]([OH:14])=[O:13])=[CH:8]1

Participants

4

Reactant 1

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

Product 1

HCID 104897874-Oxo-1,4-dihydro-2,5-quinolinedicarboxylic acid

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 14797Potassium HydroxideSolvent

Procedure

To a solution of 25 (7.90 g, 29.5 mmol) in 10% aqueous KOH solution (100 mL) was added 10% Pd/C (0.500 g). The reaction mixture was hydrogenated (50 psi) on a Parr hydrogenation apparatus at room temperature for 4 h. The catalyst was filtered off on a pad of celite and the filtrate was acidified with 2N HCl to pH=6.5, where a solid precipitated and was collected through a filtration. The solid was washed with with H2O (100 mL) and Et2O (100 mL), and dried in vacuum at 60° C. to give an off-white solid (26, 6.79 g, 98.6%). 1H NMR (DMSO-d6, 300 MHz) δ ?8.12 (d, J=8.2 Hz, 1H), 7.76 (t, J=8.2 Hz, 1H), 7.48 (d, J=8.2 Hz, 1H), 6.74 (s, 1H).

Workup

  1. customat room temperature
  2. customfor 4 h
  3. filtrationThe catalyst was filtered off on a pad of celite
  4. customprecipitated
  5. filtrationwas collected through a filtration
  6. washThe solid was washed with with H2O (100 mL) and Et2O (100 mL)
  7. customdried in vacuum at 60° C.
  8. customto give an off-white solid (26, 6.79 g, 98.6%)

Sources & evidence

ORD record
ord-55eab026457d4117afbe34dd9d82036d
Source dataset
uspto-grants-2007_09
Patent number
US07268138B2

Reaction notes

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