7-Chloro-1-ethyl-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid → 1-Ethyl-6-fluoro-7-[3-(2-furanyl)-1-piperazinyl]-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid

HRID 2165627Notes

Reaction equation

HRID 2165627 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH:6]1[CH2:11][NH:10][CH2:9][CH2:8][NH:7]1.Cl[C:13]1[CH:22]=[C:21]2[C:16]([C:17](=[O:28])[C:18]([C:25]([OH:27])=[O:26])=[CH:19][N:20]2[CH2:23][CH3:24])=[CH:15][C:14]=1[F:29]>N1C=CC=CC=1>[CH2:23]([N:20]1[C:21]2[C:16](=[CH:15][C:14]([F:29])=[C:13]([N:10]3[CH2:9][CH2:8][NH:7][CH:6]([C:2]4[O:1][CH:5]=[CH:4][CH:3]=4)[CH2:11]3)[CH:22]=2)[C:17](=[O:28])[C:18]([C:25]([OH:27])=[O:26])=[CH:19]1)[CH3:24]

Participants

4

Reactant 2

HCID 4831697-Chloro-1-ethyl-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acidHCID 167407772-(Furan-2-yl)piperazine

Product 1

HCID 148393691-Ethyl-6-fluoro-7-[3-(2-furanyl)-1-piperazinyl]-1,4-dihydro-4-oxo-3-quinolinecarboxylic acidYield 44.6%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 2.508 g of 2-(2-furanyl)piperazine, 942 mg of 7-chloro-1-ethyl-6-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid and 10 ml of pyridine was refluxed for 24 hours, then the solvent was removed. The residue was triturated with ether and chloroform, the solid collected, dissolved in 40% acetic acid and adjusted to pH 7 with 1N sodium hydroxide. The resulting solid was collected, washed with methanol and ether and dried, giving 600 mg of the desired product, mp 198° C.

Workup

  1. temperaturewas refluxed for 24 hours
  2. customthe solvent was removed
  3. customThe residue was triturated with ether and chloroform
  4. customthe solid collected
  5. dissolutiondissolved in 40% acetic acid
  6. customThe resulting solid was collected
  7. washwashed with methanol and ether
  8. customdried

Sources & evidence

ORD record
ord-74dcc025e16e4925b1c48eecf27ebacf
Source dataset
uspto-grants-1990_07
Patent number
US04940710

Reaction notes

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