Water → HCID 66917261, compound

HRID 1477146Notes

Reaction equation

HRID 1477146 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-a482a7e27ba04675a51bd866e1d52a6c
Source dataset
uspto-grants-2016_08
Patent number
US09403773B2

Reaction notes

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