Methyl iodide → HCID 22048465, compound

HRID 1830813Notes

Reaction equation

HRID 1830813 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7](=[O:12])[CH:6]=[C:5]2[C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([Cl:19])[CH:14]=1.IC.[CH3:22]COC(C)=O>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.[OH-].[Na+].C1COCC1>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]([CH3:22])[C:7](=[O:12])[CH:6]=[C:5]2[C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([Cl:19])[CH:14]=1

Participants

7

Reactant 3

HCID 6328Methyl iodideHCID 8857Ethyl AcetateHCID 12016671HCID 12016671, compound

Product 1

HCID 22048465HCID 22048465, compoundYield 86%

Reagents, catalysts & solvents 3

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 8028TetrahydrofuranSolventHCID 14798Sodium HydroxideSolvent

Procedure

A mixture of intermediate 4 (0.045 mol), iodomethane (0.225 mol) and benzyltriethylammonium chloride (0.0045 mol) in NaOH (150 ml) and THF (150 ml) was stirred overnight. EtOAc was added. The mixture was washed with water. The organic layer was separated, dried (MgSO4), filtered, and the solvent was evaporated till dryness. The residue was purified by column chromatography over silica gel (eluent: CH2Cl2/EtOAc; 95/5; 20–45 μm). The pure fractions were collected and the solvent was evaporated, yielding 13.5 g (86%) of 6-bromo-4-(3-chlorophenyl)-1-methyl-2(1H)-quinolinone (intermediate 28), melting point 182° C.

Workup

  1. washThe mixture was washed with water
  2. customThe organic layer was separated
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. customthe solvent was evaporated till dryness
  6. customThe residue was purified by column chromatography over silica gel (eluent: CH2Cl2/EtOAc; 95/5; 20–45 μm)
  7. customThe pure fractions were collected
  8. customthe solvent was evaporated

Sources & evidence

ORD record
ord-95ba0882b15f42abbeb04d66d1e13868
Source dataset
uspto-grants-2006_06
Patent number
US07067531B2

Reaction notes

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