7-Chloro-1-ethyl-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid → HCID 14839377, compound

HRID 248486Notes

Reaction equation

HRID 248486 reaction equation
[CH3:1][C:2]1[O:6][C:5]([CH:7]2[CH2:12][NH:11][CH2:10][CH2:9][NH:8]2)=[CH:4][CH:3]=1.Cl[C:14]1[CH:23]=[C:22]2[C:17]([C:18](=[O:29])[C:19]([C:26]([OH:28])=[O:27])=[CH:20][N:21]2[CH2:24][CH3:25])=[CH:16][C:15]=1[F:30]>N1C=CC=CC=1>[CH2:24]([N:21]1[C:22]2[C:17](=[CH:16][C:15]([F:30])=[C:14]([N:11]3[CH2:10][CH2:9][NH:8][CH:7]([C:5]4[O:6][C:2]([CH3:1])=[CH:3][CH:4]=4)[CH2:12]3)[CH:23]=2)[C:18](=[O:29])[C:19]([C:26]([OH:28])=[O:27])=[CH:20]1)[CH3:25]

Participants

4

Reactant 2

HCID 4831697-Chloro-1-ethyl-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acidHCID 19763586HCID 19763586, compound

Product 1

HCID 14839377HCID 14839377, compoundYield 27.6%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 4.98 g of 2-(5-methyl-2-furanyl)piperazine and 2.69 g of 7-chloro-1-ethyl-6-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid in 10 ml of pyridine was refluxed for 48 hours and then evaporated. The residue was chromatographed on silica gel eluting with chloroform:methanol:water (9.5:0.5:0.02), giving 1.1 g of the desired product, mp 186°-188° C.

Workup

  1. temperaturewas refluxed for 48 hours
  2. customevaporated
  3. customThe residue was chromatographed on silica gel eluting with chloroform:methanol:water (9.5:0.5:0.02)

Sources & evidence

ORD record
ord-6cf4322cd3364d34aa7203e04d5f98eb
Source dataset
uspto-grants-1993_05
Patent number
US05210193

Reaction notes

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