Methyl iodide → 6-(4-Chloro-benzoyl)4-(3-iodo-phenyl)-1-methyl-1H-quinolin-2-one

HRID 1597471Notes

Reaction equation

HRID 1597471 reaction equation
[Cl:1][C:2]1[CH:27]=[CH:26][C:5]([C:6]([C:8]2[CH:9]=[C:10]3[C:15](=[CH:16][CH:17]=2)[NH:14][C:13](=[O:18])[CH:12]=[C:11]3[C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([I:25])[CH:20]=2)=[O:7])=[CH:4][CH:3]=1.[OH-].[Na+].[CH3:30]I>C1COCC1.[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([C:8]2[CH:9]=[C:10]3[C:15](=[CH:16][CH:17]=2)[N:14]([CH3:30])[C:13](=[O:18])[CH:12]=[C:11]3[C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([I:25])[CH:20]=2)=[O:7])=[CH:26][CH:27]=1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 14798Sodium HydroxideHCID 154896296-(4-Chloro-benzoyl)-4-(3-iodo-phenyl)-1H-quinolin-2-one

Product 1

HCID 154896306-(4-Chloro-benzoyl)4-(3-iodo-phenyl)-1-methyl-1H-quinolin-2-oneYield 78.8%

Reagents, catalysts & solvents 2

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

6-(4-Chloro-benzoyl)-4-(3-iodo-phenyl)-1H-quinolin-2-one (63 g, 130 mMol) was dissolved in THF (500 mL) under an atmosphere of dry N2. To this solution, was added a 10 N aqueous NaOH (550 mL), benzyltriethylammonium chloride (13.8 g, 60.5 mMol) and methyl iodide (13.5 mL, 212.0 mMol). The reaction mixture was stirred at ambient temperature for 15 hours after which time it was partitioned between DCM and water. The DCM layer was successively washed with water (4 times) and then brine. The organic layer was dried over MgSO4, filtered and concentrated under vacuum to give 51.2 g of a yellow solid as the titled compound which was used without further purification.

Workup

  1. customwas partitioned between DCM and water
  2. washThe DCM layer was successively washed with water (4 times)
  3. dry with materialThe organic layer was dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-940927bbdef5492584d681dee172a8c2
Source dataset
uspto-grants-2001_09
Patent number
US06294552B1

Reaction notes

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