7-Chloro-1-ethyl-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid → HCID 14839373, compound

HRID 2165630Notes

Reaction equation

HRID 2165630 reaction equation
[Cl:1][C:2]1[S: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>[Cl:1][C:2]1[S:6][C:5]([CH:7]2[NH:8][CH2:9][CH2:10][N:11]([C:14]3[CH:23]=[C:22]4[C:17]([C:18](=[O:29])[C:19]([C:26]([OH:28])=[O:27])=[CH:20][N:21]4[CH2:24][CH3:25])=[CH:16][C:15]=3[F:30])[CH2:12]2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 4831697-Chloro-1-ethyl-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acidHCID 19763546HCID 19763546, compound

Product 1

HCID 14839373HCID 14839373, compoundYield 18.4%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 2.424 g of 2-(5-chloro-2-thienyl)piperazine and 1.076 g of 7-chloro-1-ethyl-6-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid in 12 ml of pyridine was refluxed under argon for 24 hours and then cooled. The solid was collected, washed with methanol and ether, then dried giving 320 mg of the desired product, mp 232°-234° C.

Workup

  1. temperaturewas refluxed under argon for 24 hours
  2. temperaturecooled
  3. customThe solid was collected
  4. washwashed with methanol and ether
  5. customdried

Sources & evidence

ORD record
ord-d70eaa84f75f4591b11c398df4c9ad5e
Source dataset
uspto-grants-1990_07
Patent number
US04940710

Reaction notes

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