Ethanol → HCID 66917237, compound

HRID 1477141Notes

Reaction equation

HRID 1477141 reaction equation
[F:1][C:2]1[CH:11]=[CH:10][C:9]([O:12][CH2:13][CH2:14][CH3:15])=[C:8]2[C:3]=1[C:4](=[O:26])[C:5]([C:16]1[CH:25]=[CH:24][C:19]([C:20]([O:22]C)=[O:21])=[CH:18][CH:17]=1)=[CH:6][NH:7]2.C(O)C.C1COCC1.[OH-].[Li+]>O>[F:1][C:2]1[CH:11]=[CH:10][C:9]([O:12][CH2:13][CH2:14][CH3:15])=[C:8]2[C:3]=1[C:4](=[O:26])[C:5]([C:16]1[CH:17]=[CH:18][C:19]([C:20]([OH:22])=[O:21])=[CH:24][CH:25]=1)=[CH:6][NH:7]2

Participants

6

Reactant 4

HCID 702EthanolHCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 66917193HCID 66917193, compound

Product 1

HCID 66917237HCID 66917237, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Methyl 4-(5-fluoro-4-oxo-8-propoxy-1,4-dihydroquinolin-3-yl)benzoate (330 mg, 0.93 mmol) was suspended in a mixed solvent of ethanol (3 ml) and THF (3 ml). A 1.24N lithium hydroxide aqueous solution (2 ml) was added, and the mixture was stirred at room temperature for 3 hours. Water was added to the reaction mixture, and then the resulting mixture was extracted with dichloromethane. The organic layer was washed with water, dried over magnesium sulfate, and concentrated to dryness under reduced pressure to thereby obtain 300 mg of powdery white 4-(5-fluoro-4-oxo-8-propoxy-1,4-dihydroquinolin-3-yl)benzoic acid (yield: 95%).

Workup

  1. extractionthe resulting mixture was extracted with dichloromethane
  2. washThe organic layer was washed with water
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated to dryness under reduced pressure

Sources & evidence

ORD record
ord-0963f30e8c8b49088ac3c7f0ff1cb8d3
Source dataset
uspto-grants-2016_08
Patent number
US09403773B2

Reaction notes

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