Water → HCID 22714366, compound

HRID 852278Notes

Reaction equation

HRID 852278 reaction equation
I[CH3:2].[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([CH:10]([C:29]2[N:30]=[CH:31][NH:32][CH:33]=2)[C:11]2[CH:12]=[C:13]3[C:18](=[CH:19][CH:20]=2)[N:17]([CH3:21])[C:16](=[O:22])[CH:15]=[C:14]3[C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[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:9]=[CH:8][C:7]([CH:10]([C:29]2[N:30]=[CH:31][N:32]([CH3:2])[CH:33]=2)[C:11]2[CH:12]=[C:13]3[C:18](=[CH:19][CH:20]=2)[N:17]([CH3:21])[C:16](=[O:22])[CH:15]=[C:14]3[C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[CH:6][CH:5]=1

Participants

7

Reactant 3

HCID 962WaterHCID 6328Methyl iodideHCID 178481483HCID 178481483, compound

Product 1

HCID 22714366HCID 22714366, compoundYield 42%

Reagents, catalysts & solvents 3

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 8028TetrahydrofuranSolventHCID 14798Sodium HydroxideSolvent

Procedure

Iodomethane (1.4 ml) was added to a mixture of (±)-6-[(4-chlorophenyl)-1H-imidazol-4-ylmethyl]-1-methyl-4-phenyl-2(1H)-quinolinone (7.5 g) and benzyltriethylammonium chloride (2 g) in THF (75 ml) and sodium hydroxide (75 ml) and the mixture was stirred at room temperature for 1 hour. Water was added and the mixture was extracted with ethyl acetate. The organic layer was dried, filtered off and evaporated till dryness. The residue was purified by column chromatography over silica gel (eluent: CH2Cl2/CH3OH/NH4OH 98.5/1.5/0.1). The pure fractions were collected and evaporated. Fraction 1 (3.5 g) was recrystallized from diethyl ether, yielding 3.3 g (42%) of (±)-6-[(4-chlorophenyl)(1-methyl-1H-imidazol-4-yl)methyl]-1-methyl-4-phenyl-2(1H)-quinolinone; mp. 149.9° C. (comp. 44). Fraction 2 was recrystallized from 2-propanone, methanol and diethyl ether, yielding 1.6 g (20%) of (±)-6-[(4-chlorophenyl)(1-methyl-1H-imidazol-5-yl)methyl]-1-methyl-4-phenyl-2(1H)-quinolinone (comp. 2, mp. 96.8° C.).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. customThe organic layer was dried
  3. filtrationfiltered off
  4. customevaporated till dryness
  5. customThe residue was purified by column chromatography over silica gel (eluent: CH2Cl2/CH3OH/NH4OH 98.5/1.5/0.1)
  6. customThe pure fractions were collected
  7. customevaporated
  8. customFraction 1 (3.5 g) was recrystallized from diethyl ether

Sources & evidence

ORD record
ord-e82b5378744e4726a98f06c7fd6b230b
Source dataset
uspto-grants-2007_08
Patent number
US07253183B2

Reaction notes

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