5-[3,4-Dichlorophenoxy]-6-methoxy-8-[4-phthalimido-1-methyl-butylamino]lepidine → 8-((4-Amino-1-methylbutyl)amino)-5-(3,4-dichlorophenoxy)-6-methoxy-4-methylquinoline
Reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:36]=[CH:37][C:38]=1[Cl:39])[O:5][C:6]1[C:15]([O:16][CH3:17])=[CH:14][C:13]([NH:18][CH:19]([CH3:34])[CH2:20][CH2:21][CH2:22][N:23]2C(=O)C3=CC=CC=C3C2=O)=[C:12]2[C:7]=1[C:8]([CH3:35])=[CH:9][CH:10]=[N:11]2>C(O)C>[NH2:23][CH2:22][CH2:21][CH2:20][CH:19]([NH:18][C:13]1[CH:14]=[C:15]([O:16][CH3:17])[C:6]([O:5][C:4]2[CH:36]=[CH:37][C:38]([Cl:39])=[C:2]([Cl:1])[CH:3]=2)=[C:7]2[C:12]=1[N:11]=[CH:10][CH:9]=[C:8]2[CH3:35])[CH3:34]Participants
3
Procedure
A mixture of 12.2 g of 5-(3,4-dichlorophenoxy)-6-methoxy-4-methyl-8-[(4-phthalimido-1methylbutyl)amino]quinoline (21.6 mM) and 4 ml of 98% hydrazene hydrate in 500 ml of ethanol was refluxed 5 hours. The reaction mixture was evaporated under vacuum and the residue was partitioned between 400 ml of 10% potassium hydroxide and 400 ml of ethyl acetate. The organic layer was washed twice with 300 ml of 10% potassium hydroxide then four times with water, dried with anhydrous sodium sulfate and evaporated. The residue was used in the next reaction with out further purification.
Workup
- temperaturewas refluxed 5 hours
- customThe reaction mixture was evaporated under vacuum
- customthe residue was partitioned between 400 ml of 10% potassium hydroxide and 400 ml of ethyl acetate
- washThe organic layer was washed twice with 300 ml of 10% potassium hydroxide
- dry with materialfour times with water, dried with anhydrous sodium sulfate
- customevaporated
- customThe residue was used in the next reaction with out further purification
Sources & evidence
- ORD record
- ord-81697e8ba4834ab8ad0f6d31237f659c
- Source dataset
- uspto-grants-2002_04
- Patent number
- US06376511B2
Reaction notes
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