Water → 6-(4-Chlorobenzoyl)-4-(3-methoxyphenyl)-1-methyl-2(1h)-quinolinone

HRID 2229277Notes

Reaction equation

HRID 2229277 reaction equation
[CH3:1]I.[Cl:3][C:4]1[CH:30]=[CH:29][C:7]([C:8]([C:10]2[CH:11]=[C:12]3[C:17](=[CH:18][CH:19]=2)[NH:16][C:15](=[O:20])[CH:14]=[C:13]3[C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([O:27][CH3:28])[CH:22]=2)=[O:9])=[CH:6][CH:5]=1.O>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.C1COCC1.[OH-].[Na+]>[Cl:3][C:4]1[CH:30]=[CH:29][C:7]([C:8]([C:10]2[CH:11]=[C:12]3[C:17](=[CH:18][CH:19]=2)[N:16]([CH3:1])[C:15](=[O:20])[CH:14]=[C:13]3[C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([O:27][CH3:28])[CH:22]=2)=[O:9])=[CH:6][CH:5]=1

Participants

7

Reactant 3

HCID 962WaterHCID 6328Methyl iodideHCID 227143706-(4-Chlorobenzoyl)-4-(3-methoxyphenyl)-2(1h)-quinolinone

Product 1

HCID 227143576-(4-Chlorobenzoyl)-4-(3-methoxyphenyl)-1-methyl-2(1h)-quinolinoneYield 90%

Reagents, catalysts & solvents 3

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 8028TetrahydrofuranSolventHCID 14798Sodium HydroxideSolvent

Procedure

Methyl iodide (1.58 ml) was added to a solution of interm. (5-f) (7.6 g) and benzyltriethylammonium chloride (BTEAC) (2.23 g) in THF (80 ml) and sodium hydroxide (40%, 80 ml). The mixture was stirred at room temperature for 2 hours. Water was added and the mixture was extracted with ethyl acetate. The organic layer was dried (MgSO4), filtered, and the solvent was evaporated. The residue was purified by flash column chromatography over silica gel (eluent: DCM 100%). The desired fractions were collected and the solvent was evaporated, yielding 7.1g (90%) of 6-(4-chlorobenzoyl)-4-(3-methoxyphenyl)-1-methyl-2(1H)-quinolinone (interm. 5-g).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. dry with materialThe organic layer was dried (MgSO4)
  3. filtrationfiltered
  4. customthe solvent was evaporated
  5. customThe residue was purified by flash column chromatography over silica gel (eluent: DCM 100%)
  6. customThe desired fractions were collected
  7. customthe solvent was evaporated

Sources & evidence

ORD record
ord-1273c7c5b1f44f968503912192f09300
Source dataset
uspto-grants-2002_07
Patent number
US06420387B1

Reaction notes

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