3-Acetoxy-5,5-difluoro-6-oxo-5,6-dihydro-quinoline-4-carboxylic acid methyl ester → 3-Acetoxy-5-fluoro-6-hydroxy-quinoline-4-carboxylic acid methyl ester

HRID 1422911Notes

Reaction equation

HRID 1422911 reaction equation
[CH3:1][O:2][C:3]([C:5]1[C:14]2[C:13](F)([F:15])[C:12](=[O:17])[CH:11]=[CH:10][C:9]=2[N:8]=[CH:7][C:6]=1[O:18][C:19](=[O:21])[CH3:20])=[O:4]>[Pd].CO>[CH3:1][O:2][C:3]([C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([OH:17])[C:13]=2[F:15])[N:8]=[CH:7][C:6]=1[O:18][C:19](=[O:21])[CH3:20])=[O:4]

Participants

4

Reactant 1

HCID 672472263-Acetoxy-5,5-difluoro-6-oxo-5,6-dihydro-quinoline-4-carboxylic acid methyl ester

Product 1

HCID 672473533-Acetoxy-5-fluoro-6-hydroxy-quinoline-4-carboxylic acid methyl esterYield 95%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

10% Palladium on activated carbon (178 mg, 0.17 mmol, 0.015 eq) is added at room temperature to a stirred solution of 3-acetoxy-5,5-difluoro-6-oxo-5,6-dihydro-quinoline-4-carboxylic acid methyl ester (2.27 g, 11.32 mmol, 1.0 eq) in methanol (50 mL). The resulting mixture is stirred under hydrogen flow (1 bar) at room temperature for 2 hours. The catalyst is then removed by filtration and the solution is concentrated to afford 3-acetoxy-5-fluoro-6-hydroxy-quinoline-4-carboxylic acid methyl ester as a light yellow semisolid (2.03 g, 95% yield) which is directly engaged in the next step.

Workup

  1. customThe catalyst is then removed by filtration
  2. concentrationthe solution is concentrated

Sources & evidence

ORD record
ord-26f5ceb56181434ea506401e9c3ceb5c
Source dataset
uspto-grants-2015_01
Patent number
US08927541B2

Reaction notes

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