N-[3,5-Bis(trifluoromethyl)benzyl]-2-chloro-N-methyl-4-phenyl-3-quinolinecarboxamide → N-[3,5-Bis(trifluoromethyl)benzyl]-2-methoxy-N-methyl-4-phenyl-3-quinolinecarboxamide

HRID 374993Notes

Reaction equation

HRID 374993 reaction equation
[F:1][C:2]([F:36])([F:35])[C:3]1[CH:4]=[C:5]([CH:28]=[C:29]([C:31]([F:34])([F:33])[F:32])[CH:30]=1)[CH2:6][N:7]([CH3:27])[C:8]([C:10]1[C:11](Cl)=[N:12][C:13]2[C:18]([C:19]=1[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[CH:17][CH:16]=[CH:15][CH:14]=2)=[O:9].[CH3:37][O-:38].[Na+].CO>CO>[F:1][C:2]([F:36])([F:35])[C:3]1[CH:4]=[C:5]([CH:28]=[C:29]([C:31]([F:34])([F:33])[F:32])[CH:30]=1)[CH2:6][N:7]([CH3:27])[C:8]([C:10]1[C:11]([O:38][CH3:37])=[N:12][C:13]2[C:18]([C:19]=1[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[CH:17][CH:16]=[CH:15][CH:14]=2)=[O:9]

Participants

4

Reactant 2

HCID 21463112N-[3,5-Bis(trifluoromethyl)benzyl]-2-chloro-N-methyl-4-phenyl-3-quinolinecarboxamideHCID 23694274Sodium methanolate methanol

Product 1

HCID 18996300N-[3,5-Bis(trifluoromethyl)benzyl]-2-methoxy-N-methyl-4-phenyl-3-quinolinecarboxamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of the compound obtained in Example 269 (100 mg) in methanol (2 ml) was added 28% NaOMe-methanol (2 ml), and the mixture was stirred for 3 hours with heating under reflux. The solvent was evaporated and the residue was dissolved in ethyl acetate. The solution was washed with water, dried and evaporated to yield the title compound as colorless crystals (85 mg).

Workup

  1. temperaturewith heating
  2. temperatureunder reflux
  3. customThe solvent was evaporated
  4. dissolutionthe residue was dissolved in ethyl acetate
  5. washThe solution was washed with water
  6. customdried
  7. customevaporated

Sources & evidence

ORD record
ord-adcedbdeed564bc59a2b54a8951cffdd
Source dataset
uspto-grants-1996_01
Patent number
US05482967

Reaction notes

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