Piperidine → 6-Fluoro-3-hydroxy-1-methyl-4-quinolone

HRID 358680Notes

Reaction equation

HRID 358680 reaction equation
C([O:9][C:10]1[C:19](=[O:20])[C:18]2[C:13](=[CH:14][CH:15]=[C:16]([F:21])[CH:17]=2)[N:12]([CH3:22])[CH:11]=1)(=O)C1C=CC=CC=1.N1CCCCC1>ClCCl>[F:21][C:16]1[CH:17]=[C:18]2[C:13](=[CH:14][CH:15]=1)[N:12]([CH3:22])[CH:11]=[C:10]([OH:9])[C:19]2=[O:20]

Participants

4

Reactant 2

HCID 8082PiperidineHCID 542187166-Fluoro-1-methyl-4-oxo-1,4-dihydroquinol-3-yl benzoate

Product 1

HCID 231280776-Fluoro-3-hydroxy-1-methyl-4-quinolone

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 6-fluoro-1 -methyl-4-oxo-1 ,4-dihydro-quinol-3-yl benzoate (1.90 g), piperidine (0.9 ml) and dry dichloromethane (50 ml) was stirred under nitrogen for 24 hours at ambient temperature. The solvent was removed by distillation and the residue triturated with diethyl ether (100 ml). The resultant solid was collected by filtration to give the novel compound 6-fluoro-3-hydroxy-1-methyl-4-quinolone, m.pp. 104°-106°.

Workup

  1. customThe solvent was removed by distillation
  2. customthe residue triturated with diethyl ether (100 ml)
  3. filtrationThe resultant solid was collected by filtration

Sources & evidence

ORD record
ord-21bd8084f693488d94d2a08d4c529084
Source dataset
uspto-grants-1991_03
Patent number
US04997840

Reaction notes

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