Nicotinic Acid → 3-Quinolinecarboxylic acid, 1-ethyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-, compd. with 3-pyridinecarboxylic acid (1:1)

HRID 414447

Reaction equation

HRID 414447 reaction equation
[CH3:1][CH2:2][N:3]1[C:9]2[CH:10]=[C:11]([N:15]3[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]3)[C:12]([F:14])=[CH:13][C:8]=2[C:6](=[O:7])[C:5]([C:21]([OH:23])=[O:22])=[CH:4]1.C(O)(=O)C1C=CC=NC=1>C(O)C>[C:21]([OH:23])(=[O:22])[C:5]1[CH:6]=[CH:8][CH:9]=[N:3][CH:4]=1.[CH3:1][CH2:2][N:3]1[C:9]2[CH:10]=[C:11]([N:15]3[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]3)[C:12]([F:14])=[CH:13][C:8]=2[C:6](=[O:7])[C:5]([C:21]([OH:23])=[O:22])=[CH:4]1

Participants

4

Reactant 2

HCID 938Nicotinic AcidHCID 4539Norfloxacin

Product 1

HCID 839083-Quinolinecarboxylic acid, 1-ethyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-, compd. with 3-pyridinecarboxylic acid (1:1)Yield 88%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

10 g of Norfloxacin were added to 20 ml of ethanol, the mixture obtained was then stirred and heated to reflux. 4.2 g of nicotinic acid, previously dissolved in 5 ml of hot ethanol, were added in one portion to said mixture and the resulting suspension was heated to reflux, upon which all solids dissolved. After a short time at reflux the adduct began to separate. The mixture was stirred, cooled to room temperature and finally in an ice bath to yield the nicotinic acid-Norfloxacin 1:1 adduct in 88% yield; m.p. 232°-233° C.

Workup

  1. customthe mixture obtained
  2. temperatureheated to reflux
  3. additionwere added in one portion
  4. temperaturethe resulting suspension was heated
  5. temperatureto reflux, upon which all solids
  6. dissolutiondissolved
  7. temperatureAfter a short time at reflux the adduct
  8. customto separate
  9. stirringThe mixture was stirred

Sources & evidence

ORD record
ord-d1c114c294724bda82cd49333e3ac512
Source dataset
uspto-grants-1988_12
Patent number
US04792552

Linked notes

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