8-(2-benzyloxyethoxy)-5-fluoro-3-(4-methoxyphenyl)-1H-quinolin-4-one → HCID 58492409, compound

HRID 2048000Notes

Reaction equation

HRID 2048000 reaction equation
C([O:8][CH2:9][CH2:10][O:11][C:12]1[CH:13]=[CH:14][C:15]([F:31])=[C:16]2[C:21]=1[NH:20][CH:19]=[C:18]([C:22]1[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][CH:23]=1)[C:17]2=[O:30])C1C=CC=CC=1.[H][H]>[OH-].[OH-].[Pd+2].C(O)C>[F:31][C:15]1[CH:14]=[CH:13][C:12]([O:11][CH2:10][CH2:9][OH:8])=[C:21]2[C:16]=1[C:17](=[O:30])[C:18]([C:22]1[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][CH:23]=1)=[CH:19][NH:20]2

Participants

5

Reactant 2

HCID 584924178-(2-benzyloxyethoxy)-5-fluoro-3-(4-methoxyphenyl)-1H-quinolin-4-oneHCID 178418361HCID 178418361, compound

Product 1

HCID 58492409HCID 58492409, compoundYield 105.3%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

20% palladium hydroxide/carbon (5.0 g) was added to an ethanol solution (50 ml) of 8-(2-benzyloxyethoxy)-5-fluoro-3-(4-methoxyphenyl)-1H-quinolin-4-one (6.3 g, 15.0 mmol), followed by hydrogen substitution. The mixture was stirred at room temperature for 4 hours. After completion of the reaction, the catalyst was removed and the mixture was concentrated under reduced pressure. The residue was purified using silica gel column chromatography (dichloromethane:methanol=100:0→20:1). The purified material was concentrated to dryness under reduced pressure, giving a pale yellow powder of 5-fluoro-8-(2-hydroxyethoxy)-3-(4-methoxyphenyl)-1H-quinolin-4-one (5.2 g, yield: 99%).

Workup

  1. customAfter completion of the reaction
  2. customthe catalyst was removed
  3. concentrationthe mixture was concentrated under reduced pressure
  4. customThe residue was purified
  5. concentrationThe purified material was concentrated to dryness under reduced pressure

Sources & evidence

ORD record
ord-10a28ff64c0346a08d968790fcadd348
Source dataset
uspto-grants-2013_11
Patent number
US08592593B2

Reaction notes

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