Sodium Methoxide → (4-Chlorophenyl)[4-(3-chlorophenyl)-2-methoxy-6-quinolinyl]methanone

HRID 346978Notes

Reaction equation

HRID 346978 reaction equation
[CH3:1][O-:2].[Na+].Cl.Cl[C:6]1[CH:15]=[C:14]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([Cl:22])[CH:17]=2)[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([C:23]([C:25]3[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][CH:26]=3)=[O:24])[CH:12]=2)[N:7]=1>CO>[Cl:31][C:28]1[CH:27]=[CH:26][C:25]([C:23]([C:11]2[CH:12]=[C:13]3[C:8](=[CH:9][CH:10]=2)[N:7]=[C:6]([O:2][CH3:1])[CH:15]=[C:14]3[C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([Cl:22])[CH:17]=2)=[O:24])=[CH:30][CH:29]=1

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 22385762[2-Chloro-4(3-chlorophenyl)-6-quinolinyl](4-chlorophenyl)-methanone hydrochloride

Product 1

HCID 21578663(4-Chlorophenyl)[4-(3-chlorophenyl)-2-methoxy-6-quinolinyl]methanoneYield 62%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Conditions

Temperature
80 °C

Procedure

NaOMe, 30% methanol (300 ml) was added to a mixture of intermediate (55) (0.127 mol) in methanol (285 ml) and the mixture was stirred at 80° C. for one night. The precipitate was filtered off, washed with ethanol and dried. The product (44.8 g, 87%) was taken up in DCM and the layers were separated. The organic layer was dried (MgSO4), filtered off and evaporated till dryness, yielding 32.3 g (62%) of (4-chlorophenyl)[4-(3-chlorophenyl)-2-methoxy-6-quinolinyl]-methanone (intermediate 56).

Workup

  1. filtrationThe precipitate was filtered off
  2. washwashed with ethanol
  3. customdried
  4. customthe layers were separated
  5. dry with materialThe organic layer was dried (MgSO4)
  6. filtrationfiltered off
  7. customevaporated till dryness

Sources & evidence

ORD record
ord-744b983c6a914cb590063998742017bc
Source dataset
uspto-grants-2007_02
Patent number
US07173040B2

Reaction notes

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