Water → 8-[2,6-dichloro-3-[N-(phthalimidoacetyl)-N-methylamino]benzyloxy]-2-methylquinoline
Reaction equation
[OH:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9]([CH3:12])[CH:8]=[CH:7]2.[H-].[Na+].[Cl:15][C:16]1[C:21]([N:22]([CH3:37])[C:23](=[O:36])[CH2:24][N:25]2[C:29](=[O:30])[C:28]3=[CH:31][CH:32]=[CH:33][CH:34]=[C:27]3[C:26]2=[O:35])=[CH:20][CH:19]=[C:18]([Cl:38])[C:17]=1OS(C)(=O)=O.O.[CH3:45]N(C)C=O>>[Cl:15][C:16]1[C:21]([N:22]([CH3:37])[C:23](=[O:36])[CH2:24][N:25]2[C:29](=[O:30])[C:28]3=[CH:31][CH:32]=[CH:33][CH:34]=[C:27]3[C:26]2=[O:35])=[CH:20][CH:19]=[C:18]([Cl:38])[C:17]=1[CH2:45][O:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9]([CH3:12])[CH:8]=[CH:7]2Participants
6
Reactant 5
Product 1
Procedure
To a solution of 8-hydroxy-2-methylquinoline (17.8 g) in N,N-dimethylformamide (89 ml) was added sodium hydride (40% in oil, 4.48 g) under ice-bath cooling, and the mixture was stirred for 40 minutes at ambient temperature. A solution of 2,6-dichloro-1-methylsulfonyloxy-3-[N-methyl-N-(phthalimidoacetyl)amino]benzene (56.1 g) in N,N-dimethylformamide (200 ml) was added thereto under ice-bath cooling, and the mixture was stirred for 70 minutes at ambient temperature. Water (290 ml) was dropwise added thereto, and the resulting precipitate was collected by filtration to give 8-[2,6-dichloro-3-[N-methyl-N-(phthalimidoacetyl)amino]benzyloxy]-2-methylquinoline (57.07 g). mp: 204° C.
Workup
- temperaturecooling
- temperatureunder ice-bath cooling
- stirringthe mixture was stirred for 70 minutes at ambient temperature
- filtrationthe resulting precipitate was collected by filtration
Sources & evidence
- ORD record
- ord-961490210c964e819fbc2818859a40aa
- Source dataset
- uspto-grants-1999_07
- Patent number
- US05922711
Reaction notes
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