Water → HCID 22714366, compound

HRID 564835Notes

Reaction equation

HRID 564835 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 (MgSO4), filtered off and evaporated till dryness. The residue was purified by column chromatography over silica gel (eluent: CH2Cl2CH3OH/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. dry with materialThe organic layer was dried (MgSO4)
  3. filtrationfiltered off
  4. customevaporated till dryness
  5. customThe residue was purified by column chromatography over silica gel (eluent: CH2Cl2CH3OH/NH4OH 98.5/1.5/0.1)
  6. customThe pure fractions were collected
  7. customevaporated Fraction 1 (3.5 g)
  8. customwas recrystallized from diethyl ether

Sources & evidence

ORD record
ord-cd526248a34a414796cea12e03f0b4f5
Source dataset
uspto-grants-2001_01
Patent number
US06169096A

Reaction notes

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