Sodium Hydroxide → 2-Amino-5-[4-(3,4-dimethoxybenzoyl)-1-piperazinyl]cinnamic acid
Reaction equation
[N+:1]([C:4]1[CH:14]=[CH:13][C:12]([N:15]2[CH2:20][CH2:19][N:18]([C:21](=[O:32])[C:22]3[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[C:24]([O:30][CH3:31])[CH:23]=3)[CH2:17][CH2:16]2)=[CH:11][C:5]=1[CH:6]=[CH:7][C:8]([OH:10])=[O:9])([O-])=O.[OH-].[Na+]>Cl.CO>[NH2:1][C:4]1[CH:14]=[CH:13][C:12]([N:15]2[CH2:16][CH2:17][N:18]([C:21](=[O:32])[C:22]3[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[C:24]([O:30][CH3:31])[CH:23]=3)[CH2:19][CH2:20]2)=[CH:11][C:5]=1[CH:6]=[CH:7][C:8]([OH:10])=[O:9]Participants
Procedure
2-Nitro-5-[4-(3,4-dimethoxybenzoyl)-1-piperazinyl]cinnamic acid (12 g) was dissolved in 60 ml of concentrated hydrochloric acid and to the resulting solution was added dropwise a solution of 20 g of stannous chloride in 40 ml of concentrated hydrochloric acid at room temperature. After stirring for 2 hours crystals which precipitated were collected by filtration. The crystals thus-obtained was dissolved in 240 ml of methanol and the solution was neutralized with 10% aqueous sodium hydroxide solution to precipitate crystals, which then were collected by filtration. After concentrating the methanol solution, the residue was recrystallized from ethanol to give 6.3 g of 2-amino-5-[4-(3,4-dimethoxybenzoyl)-1-piperazinyl]cinnamic acid, m.p. 168°-170.5° C., pale yellow powders.
Workup
- customprecipitated
- filtrationwere collected by filtration
- customThe crystals thus-obtained
- customto precipitate crystals, which
- filtrationthen were collected by filtration
- concentrationAfter concentrating the methanol solution
- customthe residue was recrystallized from ethanol
Sources & evidence
- ORD record
- ord-084f2b142f5a4ebe8365d579999e9838
- Source dataset
- uspto-grants-1983_11
- Patent number
- US04415572
Reaction notes
Loading…