Water → HCID 66917261, compound

HRID 2388129Notes

Reaction equation

HRID 2388129 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%).

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-5ff7048f95a240b9950c25d29447015f
Source dataset
uspto-grants-2012_09
Patent number
US08269011B2

Reaction notes

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