Methyl iodide → 4-(3-chlorophenyl)-6-(3-iodobenzoyl)-1-methyl-2(1H)-quinolinone

HRID 346985Notes

Reaction equation

HRID 346985 reaction equation
IC.[Cl:3][C:4]1[CH:5]=[C:6]([C:10]2[C:19]3[C:14](=[CH:15][CH:16]=[C:17]([C:20](=[O:28])[C:21]4[CH:26]=[CH:25][CH:24]=[C:23]([I:27])[CH:22]=4)[CH:18]=3)[NH:13][C:12](=[O:29])[CH:11]=2)[CH:7]=[CH:8][CH:9]=1.[CH3:30]COC(C)=O>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.[OH-].[Na+].C1COCC1>[Cl:3][C:4]1[CH:5]=[C:6]([C:10]2[C:19]3[C:14](=[CH:15][CH:16]=[C:17]([C:20](=[O:28])[C:21]4[CH:26]=[CH:25][CH:24]=[C:23]([I:27])[CH:22]=4)[CH:18]=3)[N:13]([CH3:30])[C:12](=[O:29])[CH:11]=2)[CH:7]=[CH:8][CH:9]=1

Participants

7

Reactant 3

HCID 6328Methyl iodideHCID 8857Ethyl AcetateHCID 210820354-(3-chlorophenyl)-6-(3-iodobenzoyl)-2(1H)-quinolinone

Product 1

HCID 210820344-(3-chlorophenyl)-6-(3-iodobenzoyl)-1-methyl-2(1H)-quinolinoneYield 45%

Reagents, catalysts & solvents 3

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 8028TetrahydrofuranSolventHCID 14798Sodium HydroxideSolvent

Procedure

Benzyltriethylammonium chloride (0.00267 mol) and iodomethane (0.053 mol) were added to a solution of intermediate (74) (0.0267 mol) in concentrated sodium hydroxide (150 ml) and THF (150 ml). The mixture was stirred at room temperature for 4 hours and poured out into ice water. EtOAc was added. The organic layer was separated, washed with water, dried (MgSO4), filtered and the solvent was evaporated. The residue was crystallized from EtOAc/2-propanone. The precipitate was filtered off and dried, yielding 6 g (45%) of 4-(3-chlorophenyl)-6-(3-iodobenzoyl)-1-methyl-2(1H)-quinolinone, melting point 235° C. (intermediate 75).

Workup

  1. customThe organic layer was separated
  2. washwashed with water
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. customthe solvent was evaporated
  6. customThe residue was crystallized from EtOAc/2-propanone
  7. filtrationThe precipitate was filtered off
  8. customdried

Sources & evidence

ORD record
ord-7b8a23354e33413db0a04447176c14ad
Source dataset
uspto-grants-2007_02
Patent number
US07173040B2

Reaction notes

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