Chloroform → N-Ethyl-N-phenyl-5-ethyl-1,2-dihydro-4-hydroxy-1-methyl-2-oxo-3-quinolinecarboxamide zinc salt
Reaction equation
[CH2:1]([N:3]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:4]([C:6]1[C:7](=[O:20])[N:8]([CH3:19])[C:9]2[C:14]([C:15]=1[OH:16])=[C:13]([CH2:17][CH3:18])[CH:12]=[CH:11][CH:10]=2)=[O:5])[CH3:2].[OH-].[Na+].C(Cl)(Cl)Cl.O.O.C([O-])(=O)C.[Zn+2:39].C([O-])(=O)C>C(O)C.O>[Zn:39].[CH2:1]([N:3]([C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1)[C:4]([C:6]1[C:7](=[O:20])[N:8]([CH3:19])[C:9]2[C:14]([C:15]=1[OH:16])=[C:13]([CH2:17][CH3:18])[CH:12]=[CH:11][CH:10]=2)=[O:5])[CH3:2]Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
N-Ethyl-N-phenyl-5-ethyl-1,2-dihydro-4-hydroxy-1-methyl-2-oxo-3-quinolinecarboxamide (1.0 g, 2.85 mmol) was dissolved in a mixture of 1M NaOH (2.95 mmol, 2.95 ml) and ethanol (6.0 ml). Chloroform (20 ml) and water (40 ml) were added followed by addition of zinc acetate dihydrate (3.0 mmol, 660 mg). The two-phase mixture was stirred vigorously for 10 min, the organic phase was separated and dried with sodium sulphate and the solvents were removed. The residue was recrystallised from methanol to give the title compound (823 mg, 76% yield). Anal. Calcd for C42H42N4O6Zn: C, 66.01; H, 5.54; N, 7.33. Found C, 65.4; H, 5.68; N, 7.29. EDTA-titriometric determination of zinc gave a content of 8.45% (theoretical content is 8.56%).
Workup
- customthe organic phase was separated
- dry with materialdried with sodium sulphate
- customthe solvents were removed
- customThe residue was recrystallised from methanol
Sources & evidence
- ORD record
- ord-ef50a015e9cc41ed93622076fd28f8f6
- Source dataset
- uspto-grants-2012_11
- Patent number
- US08314124B2
Reaction notes
Loading…