Sodium Iodide → 1-Ethyl-6,8-difluoro-1,4-dihydro-4-oxo-7-[2-(1-pyrrolidinylmethyl)morpholino]quinoline-3-carboxylic acid
Reaction equation
Cl[CH2:2][CH:3]1[CH2:8][N:7]([C:9]2[C:18]([F:19])=[C:17]3[C:12]([C:13](=[O:25])[C:14]([C:22]([OH:24])=[O:23])=[CH:15][N:16]3[CH2:20][CH3:21])=[CH:11][C:10]=2[F:26])[CH2:6][CH2:5][O:4]1.[NH:27]1[CH2:31][CH2:30][CH2:29][CH2:28]1.[I-].[Na+]>CN(C)C=O>[CH2:20]([N:16]1[C:17]2[C:12](=[CH:11][C:10]([F:26])=[C:9]([N:7]3[CH2:6][CH2:5][O:4][CH:3]([CH2:2][N:27]4[CH2:31][CH2:30][CH2:29][CH2:28]4)[CH2:8]3)[C:18]=2[F:19])[C:13](=[O:25])[C:14]([C:22]([OH:24])=[O:23])=[CH:15]1)[CH3:21]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 150 °C
Procedure
A mixture of 397 mg of 7-(2-chloromethylmorpholino)-1-ethyl-6,8-difluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid, 156 mg of pyrrolidine, 150 mg of sodium iodide and 15 ml of dimethylformamide is stirred at 150° C. for 7 hours. The reaction mixture is concentrated under reduced pressure and to the residue is added water followed by extracting with chloroform. The organic layer is washed with water, dried over anhydrous magnesium sulfate and then the solvent is distilled off to give 1-ethyl-6,8-difluoro-1,4-dihydro-4-oxo-7-[2-(1-pyrrolidinylmethyl)morpholino]quinoline-3-carboxylic acid.
Workup
- concentrationThe reaction mixture is concentrated under reduced pressure and to the residue
- additionis added water
- extractionby extracting with chloroform
- washThe organic layer is washed with water
- dry with materialdried over anhydrous magnesium sulfate
- distillationthe solvent is distilled off
Sources & evidence
- ORD record
- ord-be0c3dbdce244c3dbed9a9d058a6f0ed
- Source dataset
- uspto-grants-1989_12
- Patent number
- US04889857
Reaction notes
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