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

HRID 68162Notes

Reaction equation

HRID 68162 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-e5fb0f73a8024e808d784f64d3c305f8
Source dataset
uspto-grants-2014_09
Patent number
USRE045108E1

Reaction notes

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