Methyl iodide → HCID 22048482, compound

HRID 1830809Notes

Reaction equation

HRID 1830809 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[C:17]3[C:12](=[CH:13][CH:14]=[C:15]([CH:18]([OH:25])[C:19]4[N:23]([CH3:24])[CH:22]=[N:21][CH:20]=4)[CH:16]=3)[NH:11][C:10](=[O:26])[CH:9]=2)[CH:5]=[CH:6][CH:7]=1.IC.[CH3:29]COC(C)=O>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.C1COCC1.[OH-].[Na+]>[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[C:17]3[C:12](=[CH:13][CH:14]=[C:15]([CH:18]([OH:25])[C:19]4[N:23]([CH3:24])[CH:22]=[N:21][CH:20]=4)[CH:16]=3)[N:11]([CH3:29])[C:10](=[O:26])[CH:9]=2)[CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 3

HCID 6328Methyl iodideHCID 8857Ethyl AcetateHCID 22048484HCID 22048484, compound

Product 1

HCID 22048482HCID 22048482, compound

Reagents, catalysts & solvents 3

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 8028TetrahydrofuranSolventHCID 14798Sodium HydroxideSolvent

Procedure

A mixture of intermediate (21) (0.0132 mol), iodomethane (0.0264 mol) and benzyltriethylammonium chloride (0.00132 mol) in THF (50 ml) and sodium hydroxide 10N (50 ml) was stirred at room temperature overnight. EtOAc was added. The mixture was decanted. The organic layer was dried, filtered and the solvent was evaporated. The residue (2.9 g) was purified by column chromatography over silica gel (eluent: CH2Cl2/CH3OH/NH4OH 95/5/0.1; 15–40 μm). The pure fractions were collected and the solvent was evaporated. The residue was purified by column chromatography over silica gel (eluent: toluene/2-propanol/NH4OH 70/29/1; 15–40 μm). The pure fractions were collected and the solvent was evaporated. The residue was crystallized from diethyl ether. The precipitate was filtered off and dried, yielding 0.45 g of 4-(3-chlorophenyl)-6-[hydroxy(1-methyl-1H-imidazol-5-yl)methyl]-1-methyl-2(1H)-quinolinone, mp. 167° C. (intermediate 22).

Workup

  1. customThe mixture was decanted
  2. customThe organic layer was dried
  3. filtrationfiltered
  4. customthe solvent was evaporated
  5. customThe residue (2.9 g) was purified by column chromatography over silica gel (eluent: CH2Cl2/CH3OH/NH4OH 95/5/0.1; 15–40 μm)
  6. customThe pure fractions were collected
  7. customthe solvent was evaporated
  8. customThe residue was purified by column chromatography over silica gel (eluent: toluene/2-propanol/NH4OH 70/29/1; 15–40 μm)
  9. customThe pure fractions were collected
  10. customthe solvent was evaporated
  11. customThe residue was crystallized from diethyl ether
  12. filtrationThe precipitate was filtered off
  13. customdried

Sources & evidence

ORD record
ord-d982624099d148adb1dd48dd5c89943d
Source dataset
uspto-grants-2006_06
Patent number
US07067531B2

Reaction notes

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