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

HRID 840158Notes

Reaction equation

HRID 840158 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 benzyl-triethylammonium 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, 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 7.1 g (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. customThe organic layer was dried
  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-edb86ebc93fb4fea8e4f8e00aa86c6ec
Source dataset
uspto-grants-2002_04
Patent number
US06365600B1

Reaction notes

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