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

HRID 374994Notes

Reaction equation

HRID 374994 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][NH2:38].CO>C(O)C>[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]([NH: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 57454252Monomethylamine methanol

Product 1

HCID 21463329N-[3,5-Bis(trifluoromethyl)benzyl]-N-methyl-2-methylamino-4-phenyl-3-quinolinecarboxamide

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of the compound obtained in Example 269 (100 mg) in ethanol (4 ml) was added 40% MeNH2 -methanol (12 ml), and the mixture was stirred for 4 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 (65 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-9e6d94a7008f481ca4e4b21b9fdad631
Source dataset
uspto-grants-1996_01
Patent number
US05482967

Reaction notes

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