1-Ethyl-6,7,8-trifluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid → HCID 14839416, compound

HRID 2165691Notes

Reaction equation

HRID 2165691 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH:7]1[CH2:12][NH:11][CH2:10][CH2:9][NH:8]1.[CH2:13]([N:15]1[C:24]2[C:19](=[CH:20][C:21]([F:27])=[C:22](F)[C:23]=2[F:25])[C:18](=[O:28])[C:17]([C:29]([OH:31])=[O:30])=[CH:16]1)[CH3:14]>N1C=CC=CC=1>[CH2:13]([N:15]1[C:24]2[C:19](=[CH:20][C:21]([F:27])=[C:22]([N:11]3[CH2:10][CH2:9][NH:8][CH:7]([C:2]4[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=4)[CH2:12]3)[C:23]=2[F:25])[C:18](=[O:28])[C:17]([C:29]([OH:31])=[O:30])=[CH:16]1)[CH3:14]

Participants

4

Reactant 2

HCID 98351791-Ethyl-6,7,8-trifluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acidHCID 193868302-(Pyridin-2-yl)piperazine

Product 1

HCID 14839416HCID 14839416, compoundYield 66.7%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

The 320 mg of 2-(2-pyridinyl)piperazine, 270 mg of 1-ethyl-1,4-dihydro-6,7,8-trifluoro-4-oxo-3-quinolinecarboxylic acid and 5 ml of pyridine were stirred at 70°-80° C. for 4 hours, then cooled and the pyridine removed in vacuo. The residue was taken up in methanol and then precipitated with ether. The solid was collected and dried, giving 275 mg of the desired product, mp 222°-224° C. (dec.).

Workup

  1. temperaturecooled
  2. customthe pyridine removed in vacuo
  3. customprecipitated with ether
  4. customThe solid was collected
  5. customdried

Sources & evidence

ORD record
ord-587f1fb89cb7408796e13886787f84f2
Source dataset
uspto-grants-1990_07
Patent number
US04940710

Reaction notes

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