Piperidine → 8-Fluoro-3-hydroxy-1-methyl-4-quinolone
Reaction equation
C([O:9][C:10]1[C:19](=[O:20])[C:18]2[C:13](=[C:14]([F:21])[CH:15]=[CH:16][CH:17]=2)[N:12]([CH3:22])[CH:11]=1)(=O)C1C=CC=CC=1.N1CCCCC1>ClCCl>[F:21][C:14]1[CH:15]=[CH:16][CH:17]=[C:18]2[C:13]=1[N:12]([CH3:22])[CH:11]=[C:10]([OH:9])[C:19]2=[O:20]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A mixture of 8-fluoro-1-methyl-4-oxo-1 ,4-dihydro-quinol-3-yl benzoate (10 g), piperidine (3.18 g) and dichloromethane (200 ml) was stirred for 24 hours, a further portion of piperidine (1.7 ml) was added and the stirring continued for a further 24 hours. The solvent was removed by distillation and the residue was triturated with diethyl ether (300 ml). The resultant solid was extracted with aqueous sodium hydroxide (0.1 M, 100 ml) and the extract was neutralised with hydrochloric acid (5M, 2 ml). The resultant precipitate was collected by filtration to give the novel compound 8-fluoro-3-hydroxy-1 -methyl-4-quinolone, m.p. 248°.