Ethanol → 1-Isopropyl-2-oxo-1,2-dihydro-3-quinolinecarboxylic acid

HRID 3145

Reaction equation

HRID 3145 reaction equation
[CH:1]([N:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH:7]=[C:6]([C:14]([O:16]CC)=[O:15])[C:5]1=[O:19])([CH3:3])[CH3:2].[OH-].[Na+].C(O)C>O>[CH:1]([N:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH:7]=[C:6]([C:14]([OH:16])=[O:15])[C:5]1=[O:19])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 702EthanolHCID 14798Sodium HydroxideHCID 15468682Ethyl 1-isopropyl-2-oxo-1,2-dihydro-3-quinolinecarboxylate

Product 1

HCID 109442901-Isopropyl-2-oxo-1,2-dihydro-3-quinolinecarboxylic acidYield 88.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 1.55 g of ethyl 1-isopropyl-2(1H)-quinolone-3-carboxylate and 0.28 g of sodium hydroxide in a solvent mixture of 10 ml of ethanol and 2 ml of water was stirred at room temperature overnight. The solvent was evaporated under reduced pressure, and after addition of dil. hydrochloric acid, the precipitated solid was collected by filtration, washed with water and dried to give 1.22 g of 1-isopropyl-2(1H)-quinolone-3-carboxylic acid. m.p. 168°-169° C. (ethyl acetate)

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. additionafter addition of dil. hydrochloric acid
  3. filtrationthe precipitated solid was collected by filtration
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-0fb4566f15574ed1bc3456297724c43f
Source dataset
uspto-grants-1998_03
Patent number
US05733917

Linked notes

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