Water → HCID 66917261, compound

HRID 238341Notes

Reaction equation

HRID 238341 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[F:5][C:6]1[CH:15]=[CH:14][C:13]([O:16][CH2:17][CH2:18][CH3:19])=[C:12]2[C:7]=1[C:8](=[O:32])[C:9]([C:20]1[CH:25]=[CH:24][C:23]([O:26]C(C)C)=[CH:22][C:21]=1[O:30][CH3:31])=[CH:10][NH:11]2.O>ClCCl>[F:5][C:6]1[CH:15]=[CH:14][C:13]([O:16][CH2:17][CH2:18][CH3:19])=[C:12]2[C:7]=1[C:8](=[O:32])[C:9]([C:20]1[CH:25]=[CH:24][C:23]([OH:26])=[CH:22][C:21]=1[O:30][CH3:31])=[CH:10][NH:11]2

Participants

5

Reactant 3

HCID 962WaterHCID 6451240Aluminum(III) ChlorideHCID 66917357HCID 66917357, compound

Product 1

HCID 66917261HCID 66917261, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Aluminum chloride (108 mg, 0.81 mmol) was added to a dichloromethane solution (5 ml) of 5-fluoro-3-(4-isopropoxy-2-methoxyphenyl)-8-propoxy-1H-quinolin-4-one (120 mg, 0.31 mmol). The mixture was stirred at room temperature for 1 hour. Water and dichloromethane were added to the reaction mixture, and separated. The organic layer was then washed with water. The washed organic layer was dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was then purified by silica gel column chromatography (dichloromethane:methanol=10:1). The purified product was concentrated under reduced pressure, and the residue was recrystallized from ethyl acetate to thereby obtain 100 mg of powdery white 5-fluoro-3-(4-hydroxy-2-methoxyphenyl)-8-propoxy-1H-quinolin-4-one (yield: 90%). Melting point 251-253° C.

Workup

  1. customseparated
  2. washThe organic layer was then washed with water
  3. dry with materialThe washed organic layer was dried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was then purified by silica gel column chromatography (dichloromethane:methanol=10:1)
  6. concentrationThe purified product was concentrated under reduced pressure
  7. customthe residue was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-39f65f0adb3d48cd97f587f0df58ce7f
Source dataset
uspto-grants-2014_02
Patent number
US08642619B2

Reaction notes

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