Piperidine → 8-Fluoro-3-hydroxy-1-methyl-4-quinolone

HRID 358674Notes

Reaction equation

HRID 358674 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

HCID 8082Piperidine2×HCID 544988888-Fluoro-1-methyl-4-oxo-1,4-dihydroquinol-3-yl benzoate

Product 1

HCID 231281098-Fluoro-3-hydroxy-1-methyl-4-quinolone

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

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°.

Workup

  1. waitthe stirring continued for a further 24 hours
  2. customThe solvent was removed by distillation
  3. customthe residue was triturated with diethyl ether (300 ml)
  4. extractionThe resultant solid was extracted with aqueous sodium hydroxide (0.1 M, 100 ml)
  5. filtrationThe resultant precipitate was collected by filtration

Sources & evidence

ORD record
ord-f9b726113c9b44cd958e86b9b0386765
Source dataset
uspto-grants-1991_03
Patent number
US04997840

Reaction notes

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