Piperidine → 7-Fluoro-3-hydroxy-1-methyl-4quinolone

HRID 358666Notes

Reaction equation

HRID 358666 reaction equation
C([O:9][C:10]1[C:19](=[O:20])[C:18]2[C:13](=[CH:14][C:15]([F:21])=[CH:16][CH:17]=2)[N:12]([CH3:22])[CH:11]=1)(=O)C1C=CC=CC=1.N1CCCCC1>ClCCl>[F:21][C:15]1[CH:14]=[C:13]2[C:18]([C:19](=[O:20])[C:10]([OH:9])=[CH:11][N:12]2[CH3:22])=[CH:17][CH:16]=1

Participants

4

Reactant 2

HCID 8082PiperidineHCID 541162817-Fluoro-1-methyl-4-oxo-1,4-dihydro-quinol-3-yl benzoate

Product 1

HCID 231281077-Fluoro-3-hydroxy-1-methyl-4quinolone

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 7-fluoro-1-methyl-4-oxo-1,4-dihydro-quinol-3-yl benzoate (1 0 g), piperidine (3.7 ml) and dichloromethane (200 ml) was stirred at ambient temperature for 2 days under nitrogen. The solvent was removed by distillation at 50°. The resultant solid was triturated with diethyl ether 100 ml), collected and washed with diethyl ether (2×100 ml) to give the novel compound 7-fluoro-3-hydroxy-1 -methyl-4-quinolone, m.p. 283°-285°.

Workup

  1. customThe solvent was removed by distillation at 50°
  2. customThe resultant solid was triturated with diethyl ether 100 ml),
  3. customcollected
  4. washwashed with diethyl ether (2×100 ml)

Sources & evidence

ORD record
ord-48b4e361caff423590e18d04a35832f5
Source dataset
uspto-grants-1991_03
Patent number
US04997840

Reaction notes

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