3-(4-Acetoxy-3,5-dimethylcinnamoylamino)-4-(2-chlorophenyl)-6,8-dimethylquinoline → 3-[3-(4-Acetoxy-3,5-dimethylphenyl) propionylamino]-4-(2-chlorophenyl)-6,8-dimethylquinoline
Reaction equation
[C:1]([O:4][C:5]1[C:34]([CH3:35])=[CH:33][C:8]([CH:9]=[CH:10][C:11]([NH:13][C:14]2[CH:15]=[N:16][C:17]3[C:22]([C:23]=2[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=2[Cl:30])=[CH:21][C:20]([CH3:31])=[CH:19][C:18]=3[CH3:32])=[O:12])=[CH:7][C:6]=1[CH3:36])(=[O:3])[CH3:2]>O1CCCC1CO.[C].[Pd]>[C:1]([O:4][C:5]1[C:6]([CH3:36])=[CH:7][C:8]([CH2:9][CH2:10][C:11]([NH:13][C:14]2[CH:15]=[N:16][C:17]3[C:22]([C:23]=2[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=2[Cl:30])=[CH:21][C:20]([CH3:31])=[CH:19][C:18]=3[CH3:32])=[O:12])=[CH:33][C:34]=1[CH3:35])(=[O:3])[CH3:2]Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
5% of palladium-carbon (including 50% water, 40 mg) was added to a solution of 3-(4-acetoxy-3,5-dimethylcinnamoylamino)-4-(2-chlorophenyl)-6,8-dimethylquinoline (200 mg) in tetrahydrofuran-methanol (1:1, 5 ml). The solution was catalytically reduced at room temperature under atmospheric pressure. After the reduction, the catalyst was removed and the filtrate was concentrated to give crystals of 3-[3-(4-acetoxy-3,5-dimethylphenyl) propionylamino]-4-(2-chlorophenyl)-6,8-dimethylquinoline. The crystals were recrystallized from ethanol to afford colorless needles (146 mg, 73.0%)
Workup
- customwas catalytically reduced at room temperature under atmospheric pressure
- customAfter the reduction, the catalyst was removed
- concentrationthe filtrate was concentrated
Sources & evidence
- ORD record
- ord-6edf862a150d4536a11ca23afa1c48a2
- Source dataset
- uspto-grants-1996_06
- Patent number
- US05523407
Reaction notes
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