93106-60-6

Basic information

• Product Name: Enrofloxacin
• Synonyms: 1,4-dihydro-1-cyclopropyl-7-(4-ethyl-1-piperazinyl)-6-fluoro-4-oxo-3-quinoli;3-quinolinecarboxylicacid,1,4-dihydro-1-cyclopropyl-7-(4-ethyl-1-piperazinyl);-6-fluoro-4-oxo-;bayvp2674;cfpq;ENROFLOXACIN HCL;ROFLOXACIN BASE;enrofloxacin Baytril
• CAS NO: 93106-60-6
• Molecular Formula: C₁₉H₂₂FN₃O₃
• Molecular Weight: 359.4
• EINECS: 1806241-263-5
• Product Categories: Antibiotics for Research and Experimental Use;Biochemistry;Quinolones (Antibiotics for Research and Experimental Use);Intermediates & Fine Chemicals;Pharmaceuticals;Veterinaries;Heterocycles;API;BAYTRIL;Antibiosis
• Mol File: 93106-60-6.mol

Chemical Properties

• Melting Point: 225 °C
• Boiling Point: 560.5 °C at 760 mmHg
• Flash Point: 292.8 °C
• Appearance: Pale yellow crystals
• Density: 1.385 g/cm³
• Storage Temp.: -20°C Freezer
• Solubility: Chloroform (Slightly), Methanol (Very Slightly, Heated)
• PKA: 6.43±0.41(Predicted)
• Water Solubility: Soluble in chloroform. Slightly soluble in water. Also soluble in dilute KOH
• Merck: 14,3592
• BRN: 5307824
• CAS DataBase Reference: Enrofloxacin(CAS DataBase Reference)
• NIST Chemistry Reference: Enrofloxacin(93106-60-6)
• EPA Substance Registry System: Enrofloxacin(93106-60-6)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36/37-24/25
• WGK Germany: 3
• RTECS: VB1993650
• Hazardous Substances Data: 93106-60-6(Hazardous Substances Data)

Usage

Uses

Used in Veterinary Medicine:
Enrofloxacin is used as an antimicrobial agent for the treatment of bacterial and mycoplasma infections in animals. It is effective against both Gram-positive and Gram-negative bacteria, as well as mycoplasma, making it a valuable broad-spectrum antibiotic in veterinary practice.
Used in New Veterinary Antimicrobial Drugs:
Enrofloxacin is utilized as a component in the development of new veterinary antimicrobial drugs. Its broad-spectrum and high efficiency, coupled with its special effects on various types of bacteria, contribute to its significance in creating effective treatments for a range of bacterial infections in animals.
Brand Name:
In the United States, Enrofloxacin is marketed under the brand name Baytril, which is manufactured by Bayer. This brand name is associated with the antibiotic's use in veterinary medicine, providing a recognizable and trusted option for pet owners and veterinarians alike.

Veterinary fluoroquinolone antimicrobial agents

Enrofloxacin and sarafloxacin, danofloxacin, difloxacin, ofloxacin, norfloxacin, orbifloxacin are commonly used third-generation fluoroquinolone broad-spectrum antimicrobial agents in veterinary clinic at present , is ethyl compound of ciprofloxacin, also known as ethyl ciprofloxacin, ethyl ciprofloxacin, norfloxacin, is effective on Gram-negative bacteria, Gram-positive bacteria and mycoplasma, its antibacterial activity is significantly superior to norfloxacin, the effect on mycoplasma is stronger than tylosin and Tiamulin Fumarate. This product is oral, intramuscular and subcutaneous injection, and is easily absorbed, widely distributed in vivo, in addition to the central nervous system, the concentration of the drug in other organizations, almost all are higher than the blood concentration. De ethylation in vivo, mainly produced active metabolite ciprofloxacin, but different among the animals metabolism are larger, birds, dogs, rabbits and cattle body's metabolic rates are high, horses and pigs body's metabolic rates are lower. Clinically Enrofloxacin is used for the treatment of various mycoplasma disease, and respiratory system, digestive system and urogenital system infections, skin infections and sepsis caused by E. coli, Salmonella, Haemophilus, Erysipelas bacillus, Staphylococcus, Streptococcus etc. Especially suitable for mixing infections caused by a variety of bacteria. Spatial structure formulae diagram of Enrofloxacin The above information is edited by the lookchem of Liu Yujie.

Reasonable compatibility

1. Cooperated application of Enrofloxacin with aminoglycoside (gentamicin), third-generation cephalosporins (cefotaxime, ceftriaxone) and penicillin, colistin, may have synergistic antibacterial effect on certain bacteria (especially Pseudomonas aeruginosa or Enterobacteriaceae), in addition to penicillin-type drugs, due to enhanced toxicity, when in combination, need to reduce the dose, and administered separately. 2. Antibacterial activity of Enrofloxacin combined with apramycin enhanced, showed a synergistic effect. The reason was that antibacterial mechanism of apramycin was to specifically hinder biosynthesis of bacterial protein, and thus achieved effect on inhibiting and killing bacteria, while Enrofloxacin could specifically act on subunit A of bacterial DNA gyrase, inhibiting its activity, affecting DNA melting and sealing chain, both of combination had double blocking effect on bacterial replication and translation process. 3. at the same day were successively mixed to drink with colistin sulfate, can improve the efficacy of Enrofloxacin on chicken bacterial disease. and compatibility with SD silver used for the topical treatment of otitis in dogs. Reference data: Zheng Hugong, Cui Yaoming editor. reasonable compatibility use of veterinary, Zhengzhou: Henan Science and Technology Press, 2009.

Incompatibility

1. Enrofloxacin can inhibit metabolism of theophylline and caffeine, make the blood concentration increase, thereby causing toxic reactions. 2. Combined with anticholinergic drugs (atropine, 654-2) and H2 receptor antagonists (cimetidine, famotidine), making the bioavailability of Enrofloxacin reduce. 3. Enrofloxacin has a role in inhibiting liver drug enzymes, in combination with drugs metabolized in the liver such as erythromycin, lincomycin, etc. making its clearance decrease, blood concentration increased. 4. antacids may reduce absorption of Enrofloxacin in the gastrointestinal tract, not suitable for simultaneous use. 5. mixed with strongly acidic liquid and the strong alkaline liquid and precipitated. 6. Enrofloxacin and metoclopramide occur chemical changes, easy to turn into muddy, should not be mixed injection.

Side effects

Toxicity of Enrofloxacin is less, safe for clinical use. Therapeutic doses have non-teratogenic and mutagenic effect. Can make young animals cartilage occur turbid, causing lameness and pain. Digestive system reactions are vomiting, abdominal pain and bloating. Skin reactions are erythema, pruritus, urticaria and photosensitivity reactions, etc.

Precautions

1. Enrofloxacin aqueous solution was met with light and easy to change color and decompose, should be kept in dark place. 2. Drug-resistant strains of the product showed an increasing trend, not used at sub-therapeutic doses for long-term. 3. Antacids can inhibit the absorption of this product, should be avoided drinking at the same time. 4. In clinical application, can appropriately adjust dosage based on disease, concentration range of drinking water in poultry, per liter of water, added 25 to 100 mg. 5. withdrawal period of chicken is 8 days. Disabled in egg producing period of laying hen. 6. chicks are very sensitive to Enrofloxacin injection, had many poisoning report, the dose should be strictly controlled.

Veterinary Drugs and Treatments

Enrofloxacin is approved for use in dogs and cats (oral only) for the management of diseases associated with bacteria susceptible to enrofloxacin. Because of the dosage restriction (5 mg/kg) for cats, enrofloxacin is generally used in this species only for the most susceptible bacterial infections. It is also been approved for use in cattle (not dairy cattle or veal calves).

InChI:InChI=1/C19H22FN3O3/c1-2-21-5-7-22(8-6-21)17-10-16-13(9-15(17)20)18(24)14(19(25)26)11-23(16)12-3-4-12/h9-12H,2-8H2,1H3,(H,25,26)

Synthetic route

4-ethylpiperazine (5308-25-8) + 7-chloro-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-3-quinoline carboxylic acid (86393-33-1) → enrofloxacin (93106-60-6)

Conditions	Yield
With nano iron oxide on ZrO2 coated sulfonic acid In water for 0.316667h; Solvent; Temperature; Reagent/catalyst; Reflux;	97%
at 150℃; for 0.416667h; Microwave irradiation;	93%
With aluminum tri-bromide In ethanol at 75℃; for 4h; Reagent/catalyst; Solvent; Temperature;	92%

1-cyclopropyl-6-fluoro-7-chloro-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid sodium salt + 4-ethylpiperazine (5308-25-8) → enrofloxacin (93106-60-6)

Conditions	Yield
With aluminum (III) chloride In i-Amyl alcohol at 140℃; for 8h; Temperature;	91.8%

ditrimethylsilyl N-cyclopropyl-3-(4-ethyl-1-piperazinyl)anilinomethylenemalonate (131776-44-8) → enrofloxacin (93106-60-6)

Conditions	Yield
	90%

4-ethylpiperazine (5308-25-8) + 7-chloro-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-3-quinoline carboxylic acid (86393-33-1) → 7-chloro-1-cyclopropyl-6-(4-ethyl-piperazin-1-yl)-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid + enrofloxacin (93106-60-6)

Conditions	Yield
In water for 13h; Heating;	A n/a B 89%

ethyl bromide (74-96-4) + ciprofloxacin hydrochloride (93107-08-5) → enrofloxacin (93106-60-6)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine; potassium iodide In water; acetonitrile at 20℃; for 12h;	70%

4-ethylpiperazine (5308-25-8) + ethyl 2,4,5-trifluorobenzoylacetate (98349-24-7) + N,N-dimethyl-formamide dimethyl acetal (4637-24-5) + Cyclopropylamine (765-30-0) → enrofloxacin (93106-60-6)

Conditions	Yield
Yield given. Multistep reaction;

ethyl 2,4-dichloro-5-fluoro-benzoyl-acetate (86483-51-4) → enrofloxacin (93106-60-6)

Conditions	Yield
Multi-step reaction with 5 steps 1: acetic anhydride / 2 h / Heating 2: 92 percent / ethanol / 1 h / Ambient temperature 3: 90 percent / potassium carbonate / dimethylformamide / 2 h / 140 - 150 °C 4: 93 percent / conc. H2SO4 / H2O / 1.5 h / Heating 5: 86 percent / dimethylsulfoxide / 2.5 h / 140 °C View Scheme

3-Cyclopropylamino-2-(2,4-dichlor-5-fluorbenzoyl)acrylsaeure-ethylester (86483-53-6) → enrofloxacin (93106-60-6)

Conditions	Yield
Multi-step reaction with 3 steps 1: 90 percent / potassium carbonate / dimethylformamide / 2 h / 140 - 150 °C 2: 93 percent / conc. H2SO4 / H2O / 1.5 h / Heating 3: 86 percent / dimethylsulfoxide / 2.5 h / 140 °C View Scheme

ethyl 1-cyclopropyl-7-chloro-6-fluoro-1,4-dihydro-4-oxo-3-quinoline-carboxylate (86483-54-7) → enrofloxacin (93106-60-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: 93 percent / conc. H2SO4 / H2O / 1.5 h / Heating 2: 86 percent / dimethylsulfoxide / 2.5 h / 140 °C View Scheme

2,4-dichloro-5-fluorobenzoyl chloride (86393-34-2) → enrofloxacin (93106-60-6)

Conditions	Yield
Multi-step reaction with 4 steps 1: 62 percent / pyridine / dioxane / 1.) 2 h, room temperature, 2.) 1 h, 70 - 80 deg C. 2: 85 percent / potassium carbonate / dimethylformamide / 2 h / 140 - 150 °C 3: 92 percent / conc. H2SO4 / H2O; acetic acid / 1.5 h / Heating 4: 86 percent / dimethylsulfoxide / 2.5 h / 140 °C View Scheme
Multi-step reaction with 7 steps 1: Mg/ethanol, CCl4 / ethanol; toluene / 1.) 0 to -5 deg C, 2.) 12 h, room temperature 2: p-toluenesulfonic acid / H2O / 5 h / Heating 3: acetic anhydride / 2 h / Heating 4: 92 percent / ethanol / 1 h / Ambient temperature 5: 90 percent / potassium carbonate / dimethylformamide / 2 h / 140 - 150 °C 6: 93 percent / conc. H2SO4 / H2O / 1.5 h / Heating 7: 86 percent / dimethylsulfoxide / 2.5 h / 140 °C View Scheme
Multi-step reaction with 2 steps 1.1: tributyl-amine / 1 h / 70 °C 1.2: 15 °C / 1520.1 Torr 2.1: cesium hydroxide / 5,5-dimethyl-1,3-cyclohexadiene / 125 - 130 °C 2.2: 8 h / 85 °C View Scheme

3-Cyclopropylamino-2-(2,4-dichlor-5-fluorbenzoyl)acrylsaeure-methylester (105392-26-5) → enrofloxacin (93106-60-6)

Conditions	Yield
Multi-step reaction with 3 steps 1: 85 percent / potassium carbonate / dimethylformamide / 2 h / 140 - 150 °C 2: 92 percent / conc. H2SO4 / H2O; acetic acid / 1.5 h / Heating 3: 86 percent / dimethylsulfoxide / 2.5 h / 140 °C View Scheme

7-chloro-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-quinoline-3-carboxylic acid methyl ester (104599-90-8) → enrofloxacin (93106-60-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: 92 percent / conc. H2SO4 / H2O; acetic acid / 1.5 h / Heating 2: 86 percent / dimethylsulfoxide / 2.5 h / 140 °C View Scheme

diethyl 2,4-dichloro-5-fluoro-benzoyl-malonate (86483-50-3) → enrofloxacin (93106-60-6)

Conditions	Yield
Multi-step reaction with 6 steps 1: p-toluenesulfonic acid / H2O / 5 h / Heating 2: acetic anhydride / 2 h / Heating 3: 92 percent / ethanol / 1 h / Ambient temperature 4: 90 percent / potassium carbonate / dimethylformamide / 2 h / 140 - 150 °C 5: 93 percent / conc. H2SO4 / H2O / 1.5 h / Heating 6: 86 percent / dimethylsulfoxide / 2.5 h / 140 °C View Scheme

3-(Cyclopropylamino)acrylsaeure-methylester (72396-25-9) → enrofloxacin (93106-60-6)

Conditions	Yield
Multi-step reaction with 4 steps 1: 62 percent / pyridine / dioxane / 1.) 2 h, room temperature, 2.) 1 h, 70 - 80 deg C. 2: 85 percent / potassium carbonate / dimethylformamide / 2 h / 140 - 150 °C 3: 92 percent / conc. H2SO4 / H2O; acetic acid / 1.5 h / Heating 4: 86 percent / dimethylsulfoxide / 2.5 h / 140 °C View Scheme

2,4-dichloro-alpha(elhoxymethlene)-5-fluoro-beta-oxo-benzene propanoic acid ethyl ester (86483-52-5) → enrofloxacin (93106-60-6)

Conditions	Yield
Multi-step reaction with 4 steps 1: 92 percent / ethanol / 1 h / Ambient temperature 2: 90 percent / potassium carbonate / dimethylformamide / 2 h / 140 - 150 °C 3: 93 percent / conc. H2SO4 / H2O / 1.5 h / Heating 4: 86 percent / dimethylsulfoxide / 2.5 h / 140 °C View Scheme

4-ethylpiperazine (5308-25-8) + 3-Cyclopropylamino-2-(2,4-dichlor-5-fluorbenzoyl)acrylsaeure-ethylester (86483-53-6) → enrofloxacin (93106-60-6)

Conditions	Yield
Stage #1: 3-Cyclopropylamino-2-(2,4-dichlor-5-fluorbenzoyl)acrylsaeure-ethylester With cesium hydroxide In 5,5-dimethyl-1,3-cyclohexadiene at 125 - 130℃; Stage #2: 4-ethylpiperazine With aluminum (III) chloride In ethanol at 85℃; for 8h; Solvent; Reagent/catalyst; Temperature;	48.7 g

enrofloxacin (93106-60-6) → 1-cyclopropyl-7-(4-ethyl-1-piperazinyl)-6-fluoro-1,4-dihydro-4-oxo-quinolinoyl chloride (474022-78-1)

Conditions	Yield
With thionyl chloride for 10h; Heating;	95.1%
With thionyl chloride at 75℃; for 10h;
With thionyl chloride at 70℃;

C6H16Cl4Cu2N8O2 + enrofloxacin (93106-60-6) → C22H29CuFN7O4(1+)*Cl(1-)

Conditions	Yield
With sodium hydroxide In methanol at 20℃; for 2h;	88%

enrofloxacin (93106-60-6) + 1,1'-carbonyldiimidazole (530-62-1) → 1-cyclopropyl-6-fluoro-7-(4-ethylpiperazin-1-yl)-3-(1H-imidazole-1-formyl)-quinoline-4(1H)-one

Conditions	Yield
In acetonitrile Solvent; Reflux;	86.4%

enrofloxacin (93106-60-6) → C38H50CaF2N6O10

Conditions	Yield
With water; calcium hydroxide In methanol at 40℃; for 8h; Temperature; Solvent;	85%

1,10-Phenanthroline (66-71-7) + nickel(II) chloride hexahydrate + enrofloxacin (93106-60-6) → [Ni(enx)2(1,10-phenantroline)]

Conditions	Yield
With hydrogenchloride; potassium hydroxide In ethanol for 2h; pH=7;	85%

1,10-Phenanthroline (66-71-7) + cobalt(II) chloride hexahydrate + enrofloxacin (93106-60-6) → [Co(enx)2(1,10-phenantroline)]

Conditions	Yield
With hydrogenchloride; potassium hydroxide In ethanol for 2h; pH=7;	82%

8-quinolinol (148-24-3) + nickel(II) chloride hexahydrate + enrofloxacin (93106-60-6) → [Ni(enx)2(1,10-phenantroline)(Q)]

Conditions	Yield
With hydrogenchloride; potassium hydroxide In ethanol for 2h; pH=7; Reflux;	80%

8-quinolinol (148-24-3) + cobalt(II) chloride hexahydrate + enrofloxacin (93106-60-6) → C28H27CoFN4O4*H2O

Conditions	Yield
With hydrogenchloride; potassium hydroxide In ethanol for 1h; pH=7; Reflux;	80%

8-quinolinol (148-24-3) + nickel(II) chloride hexahydrate + enrofloxacin (93106-60-6) → C28H27FN4NiO4*H2O

Conditions	Yield
With hydrogenchloride; potassium hydroxide In ethanol for 1h; pH=7; Reflux;	78%

vanadium(V) oxychloride (7727-18-6) + enrofloxacin (93106-60-6) + o-toluidine (95-53-4) → bis[1-cyclopropyl-7-(4-ethyl-piperazin-1-yl)-6-fluoro-4-oxo-1,4-dihydro-quinoline-3-carboxylato]4-(4-amino-3-methylphenyl)-2-methylanilineoxo vanadium chloride monohydrate

Conditions	Yield
Stage #1: vanadium(V) oxychloride; enrofloxacin With sodium hydroxide In ethanol at 20℃; for 1h; Stage #2: o-toluidine In ethanol at 20℃; for 72h;	77%

zinc(II) perchlorate + enrofloxacin (93106-60-6) → C57H63F3N9O9Zn(1-)

Conditions	Yield
With ammonium hydroxide In methanol; water for 0.166667h;	77%

1,2,3-Benzotriazole (95-14-7) + enrofloxacin (93106-60-6) → 3-(1H-benzo[d][1,2,3]triazole-1-carbonyl)-1-cyclopropyl-7-(4-ethylpiperazin-1-yl)-6-fluoroquinolin-4(1H)-one (1381763-39-8)

Conditions	Yield
With thionyl chloride In dichloromethane at 20℃;	76%

enrofloxacin (93106-60-6) + isopropylamine (75-31-0) → 1-cyclopropyl-7-(4-ethylpiperazin-1-yl)-6-fluoro-1,4-dihydro-4-oxo-N-(propan-2-yl)quinoline-3-carboxamide

Conditions	Yield
With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 0 - 20℃;	76%

vanadium(V) oxychloride (7727-18-6) + enrofloxacin (93106-60-6) + triethylamine (121-44-8) → bis[1-cyclopropyl-7-(4-ethyl-piperazin-1-yl)-6-fluoro-4-oxo-1,4-dihydro-quinoline-3-carboxylato]N,N-diethylethanamineoxo vanadium chloride hexahydrate

Conditions	Yield
Stage #1: vanadium(V) oxychloride; enrofloxacin With sodium hydroxide In ethanol at 20℃; for 1h; Stage #2: triethylamine In ethanol at 20℃; for 72h;	76%

bis(acetylacetonato)dioxidomolybdenum(VI) + enrofloxacin (93106-60-6) → MoO2(1-cyclopropyl-7-(4-ethylpiperazin-1-yl)-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylate)2

Conditions	Yield
With potassium hydroxide In methanol a MeOH soln. of 2 equiv. of F-compd. deprotonated with 2 equiv. of KOH was added to the Mo-compd. soln. in MeOH, reflux for 2.5 h; soln. was filtered and left to slowly evaporate for a few days, crystalswere filtered off, washed with MeOH and dried, elem. anal.;	75%

manganese(II) chloride tetrahydrate + enrofloxacin (93106-60-6) → Mn(1-cyclopropyl-7-(4-ethyl-piperazin-1-yl)-6-fluoro-4-oxo-1,4-dihydro-quinoline-3-carboxylato)2(H2O)2 (1030834-09-3)

Conditions	Yield
With potassium hydroxide In methanol a soln. of ligand deprotonated with KOH, added to a soln. of Mn salt, refluxed for 2 h; filtered, crystd. for days, filtered, washed (MeOH), dried; elem. anal.;	75%

zinc(II) nitrate hexahydrate + (4S)-4-isopropyl-N-[(4R)-4-isopropyl-4,5-dihydro-1,3-oxazol-2-yl]-N-(4-vinylbenzyl)-4,5-dihydro-1,3-oxazol-2-amine + water (7732-18-5) + enrofloxacin (93106-60-6) → C40H50FN6O5Zn(1+)*NO3(1-)

Conditions	Yield
With sodium hydroxide In acetonitrile	75%

C20H28Cl4Cu2N8O2 + enrofloxacin (93106-60-6) → C29H35CuFN7O4(1+)*Cl(1-)

Conditions	Yield
With sodium hydroxide In methanol at 20℃; for 2h;	74.1%

vanadium(V) oxychloride (7727-18-6) + enrofloxacin (93106-60-6) + N,N-dimethyl-formamide (68-12-2, 33513-42-7) → bis[1-cyclopropyl-7-(4-ethyl-piperazin-1-yl)-6-fluoro-4-oxo-1,4-dihydro-quinoline-3-carboxylato]N,N-dimethylformamideoxo vanadium chloride pentahydrate

Conditions	Yield
Stage #1: vanadium(V) oxychloride; enrofloxacin With sodium hydroxide In ethanol at 20℃; for 1h; Stage #2: N,N-dimethyl-formamide In ethanol at 20℃; for 72h;	74%

pyridine (110-86-1) + vanadium(V) oxychloride (7727-18-6) + enrofloxacin (93106-60-6) → bis[1-cyclopropyl-7-(4-ethyl-piperazin-1-yl)-6-fluoro-4-oxo-1,4-dihydro-quinoline-3-carboxylato]pyridineoxo vanadium chloride tetrahydrate

Conditions	Yield
Stage #1: vanadium(V) oxychloride; enrofloxacin With sodium hydroxide In ethanol at 20℃; for 1h; Stage #2: pyridine In ethanol at 20℃; for 72h;	73%

boron trifluoride diethyl etherate (109-63-7) + enrofloxacin (93106-60-6) → difluoroboron complexes of enrofloxacin

Conditions	Yield
In dichloromethane; N,N-dimethyl-formamide for 24h; Reflux;	71%

cobalt(II) chloride hexahydrate + enrofloxacin (93106-60-6) → Co(1-cyclopropyl-7-(4-ethyl-piperazin-1-yl)-6-fluoro-4-oxo-1,4-dihydro-quinoline-3-carboxylato)2(H2O)2 (1030834-12-8)

Conditions	Yield
With potassium hydroxide In methanol a soln. of ligand deprotonated with KOH, added to a soln. of Co salt, refluxed; filtered, crystd., filtered, washed (MeOH), dried; elem. anal.;	70%

pyridine (110-86-1) + methanol (67-56-1) + water (7732-18-5) + enrofloxacin (93106-60-6) + zinc(II) chloride (7646-85-7) → bis(enrofloxacinato)bis(pyridine)zinc(II) hexahydrate monomethanolate

Conditions	Yield
With KOH In methanol KOH added to MeOH soln. of enrofloxacin; added to MeOH soln. of ZnCl2; pyridine added; crystd. by slow evapn. after 10 d; elem. anal.;	70%

[2,2]bipyridinyl (366-18-7) + enrofloxacin (93106-60-6) + zinc(II) chloride (7646-85-7) → [Zn(erx)(bipy)Cl] (1426910-55-5)

Conditions	Yield
Stage #1: enrofloxacin With potassium hydroxide In methanol at 20℃; for 0.333333h; Stage #2: [2,2]bipyridinyl; zinc(II) chloride In methanol	70%

methanol (67-56-1) + 1,10-Phenanthroline (66-71-7) + manganese(II) chloride tetrahydrate + enrofloxacin (93106-60-6) → [Mn(enrofloxacinato)2(1,10-phenanthroline)]*1.5MeOH*H2O

Conditions	Yield
Stage #1: methanol; enrofloxacin With potassium hydroxide for 0.5h; Stage #2: methanol; 1,10-Phenanthroline; manganese(II) chloride tetrahydrate for 1h;	70%

Upstream product

• 5308-25-8 4-ethylpiperazine 
• 86393-33-1 7-chloro-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-3-quinoline carboxylic acid 
• 98349-24-7 ethyl 2,4,5-trifluorobenzoylacetate 
• 4637-24-5 N,N-dimethyl-formamide dimethyl acetal 
• 765-30-0 Cyclopropylamine 
• 86483-53-6 3-Cyclopropylamino-2-(2,4-dichlor-5-fluorbenzoyl)acrylsaeure-ethylester 
• 74-96-4 ethyl bromide 
• 93107-08-5 ciprofloxacin hydrochloride 
• 131776-44-8 ditrimethylsilyl N-cyclopropyl-3-(4-ethyl-1-piperazinyl)anilinomethylenemalonate 
• 86483-52-5 2,4-dichloro-alpha(elhoxymethlene)-5-fluoro-beta-oxo-benzene propanoic acid ethyl ester 
• 72396-25-9 N-(Cyclopropylamino)acrylsaeure-methylester 
• 86483-50-3 diethyl 2,4-dichloro-5-fluoro-benzoyl-malonate 
• 104599-90-8 7-chloro-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-quinoline-3-carboxylic acid methyl ester 
• 105392-26-5 3-Cyclopropylamino-2-(2,4-dichlor-5-fluorbenzoyl)acrylsaeure-methylester 

Downstream Products

• 1275596-12-7 CuCl(enrofloxacin(-1H))(2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline) 
• 149091-97-4 M₁-Enrofloxacin 
• 85721-33-1 ciprofloxacin 
• 109142-50-9 1-cyclopropyl-6-fluoro-1,4-dihydro-7-(4-hydroxypiperazin-1-yl)-4-oxoquinoline-3-carboxylic acid 
• 105674-91-7 1-cyclopropyl-6-fluoro-7-amino-1,4-dihydro-4-oxoquinoline-3-carboxylic acid 
• 1421369-57-4 C₁₉H₂₁FN₃O₃^(1-)*Cu⁽²⁺⁾*Cl^(1-)*C₁₁H₁₆N₄ 

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Purpose: To evaluate pharmacological properties (antibacterial activity; accumulation in phagocytic cells; activity against intracellular bacteria; susceptibility to fluoroquinolone efflux transporters) of ciprofloxacin derivatives modified at C-7 of the

Preparation method of quinolone carboxylic acid derivative or phthalazinone carboxylic acid derivative

The invention belongs to the field of pharmaceutical chemicals, relates to a preparation method of a quinolone carboxylic acid derivative or a phthalazinone carboxylic acid derivative, and particularly relates to a preparation method of a 7-substituted-3-quinolone carboxylic acid derivative or a 7-substituted-1,5-phthalazinone carboxylic acid derivative. The preparation method comprises the following steps: (1) in an organic solvent, carrying out coupling reaction on a boron chelate II and organic amine III in the presence of an organosilicon compound to obtain a compound IV; and (2) mixing the compound IV with hydrochloric acid, and then filtering and separating the precipitated compound I. Compared with conventional methods, the preparation method provided by the invention has the advantages that the conditions are milder, the hydrolysis of the substrate quinoline carboxylic acid boric acid ester can be reduced, and meanwhile, the influence of a byproduct HF on the product purity is avoided. The method is high in yield and high in purity; compared with the traditional alkali, the organic silicon is more suitable for industrial preparation of the 7-substituted-3-quinolone carboxylic acid derivative or the 7-substituted-1,5-phthalazinone carboxylic acid derivative.

A norfloxacin, ciprofloxacin and enrofloxacin synthetic method

The present invention provides a norfloxacin, ciprofloxacin and enrofloxacin preparation method, which comprises the carboxylic acid and piperazine in the solvent under the catalytic action of the catalyst in the reaction step, the catalyst is AlBr3 , FeBr3 , ZnBr2 , CuBr2 Or SnBr4 , It has high yield, low cost and the advantage of energy saving and emission reduction.

Nano-Fe3 O4@ZrO2-SO3 H as highly efficient recyclable catalyst for the green synthesis of fluoroquinolones

Nano-Fe3 O4 @ZrO2-SO3 H (n-FZSA), was utilized as a magnetic catalyst for the synthesis of various fluoroquinolone compounds. These compounds were prepared by the direct amination of 7-halo-6-fluoroquinolone-3-carboxylic acids with piperazine derivatives and (4aR,7aR)-octahydro-1H-pyrrolo[3,4-b] pyridine in water. The results showed that n-FZSA exhibited high catalytic activity towards the synthesis of fluoroquinolone derivatives, giving the desired products in high yields. Furthermore, the catalyst was recyclable and could be used at least seven times without any discernible loss in its catalytic activity. Overall, this new catalytic method for the synthesis of fluoroquinolone derivatives provides rapid access to the desired compounds in refluxing water following a simple work-up procedure, and avoids the use of organic solvents.

A norfloxacin, ciprofloxacin and enrofloxacin preparation method

The invention discloses a preparation method of norfloxacin, ciprofloxacin and enrofloxacin. The preparation method comprises the following steps: directly reacting 1-ethyl-6-fluoro-7-chlo-4-oxo-1,4-dihydro-quinoline-3-carboxylate or 1-cyclopropyl-6-fluoro-7-chlo-4-oxo-1,4-dihydro-quinoline-3-carboxylate with piperazine (or N-ethyl piperazine); and then, performing after-treatment to prepare a corresponding target product norfloxacin (or ciprofloxacin or enrofloxacin). The preparation method disclosed by the invention is short in reaction step, convenient to operate, less investment and beneficial to industrial production; consumption of piperazine (or N-ethyl piperazine) can be reduced by more than half; under the catalytic action, the reaction temperature is low, the byproducts are less, the yield is high and the cost is low; heavy use of inorganic acid and inorganic alkaline is avoided, so that the pollution is reduced.

Conventional and microwave-assisted synthesis of quinolone carboxylic acid derivatives

Various antibacterial fluoroquinolone compounds are synthesized by the direct amination of 7-halo-6-fluoroquinolone-3-carboxylic acids with a variety of piperazine derivatives and (4aR,7aR)-octahydro-1H-pyrrolo[3,4-b]pyridine using microwave under different reaction conditions. Solvent free high yield microwave synthesis of antibacterial fluoroquinolone compounds is convenient, rapid and environmentally friendly method.

NOVEL METHOD OF SYNTHESIS OF FLUOROQUINOLONES

The invention relates to a method of preparation of fluoroquinolones of formula (I) from compounds of formula (II): in which R1, R2, R3, R4, R5, R6, R7, and X are as defined in Claim 1.

Convenient one pot synthesis of some fluoroquinolones in aqueous media

A one pot synthetic strategy for the preparation of fluoroquinolones from 1 is introduced. Product 3 was condensed with piperazine in an aqueous media to produce pharmaceutical grade ciprofloxacin in 86% yield. The method was extended to the synthesis of some other fluoroquinolones with pharmaceutical grade quality.

Process for the preparation of quinolone derivatives

This invention relates to an improved process for the preparation of quinolone drugs of the formula (I), wherein R=C1-C6 alkyl, C3-C6 cycloalklyl, aryl, substituted aryl, NR1R2=diarylamino, arylalkylamino, C1-C6-dialkylamino, piprazinyl, N or C alkyl (C1-C6) substituted piperazinyl, morpholino, pyrrolidinyl, substituted pyrrolidinyl, aralkyl, substituted aralkyl etc. Some of the compounds falling within the formula (I) are ciprofloxacin, enrofloxin, pefloxacin, etc. These compounds are useful as antibacterial drugs. The process of the present invention for preparation of compound of formula (I) comprises in enhancing the reactivity of the displaceable halogen (X) in the compound of the formula (II) towards various amines of formula (III) wherein R=as defined for compound of formula (I), R3=COOR6 (R6=C1-C6 alkyl, aryl, aralkyl), nitrile a carboxamide (—CONR7R8, R7 and R8=C1-C6 alkyl, C3-C6 cycloalkyl, aralkyl), X=Cl, Br, F; NR1R2=as defined above by introducing a nitro group ortho to the displaceable halo group and subsequently removing the nitro group in a conventional manner. The process of the present invention enhances the yield of the compound of the formula (I) and also improves the quality of the prepared compound.

Molecular structures of new ciprofloxacin derivatives

Two new derivatives from the ciprofloxacin fluoroquinoline family, 7-chloro-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo- quinoline-3-methylcarbamate and 1-cyclopropyl-7-(4-ethyl-1-piperazinyl)-6-fluoro-1,4-dihydro-(3-oxopyrazolo) [4,3-c]quinoline, were synthesised, tested for antibacterial activity and crystallised. Their molecular and crystal structures were determined. Tests in vitro reveal lower activities than for ciprofloxacin. Characteristic structural features of these compounds are comparable to data for other known fluoroquinolines. The bicyclic quinoline ring is planar in both compounds; the carbamate side chain and five-membered pyrazolo ring are almost coplanar with it. A piperazinyl ring exhibits a chair conformation. In the crystal packing of the carbamate analogue, two C-HO interactions form a dimer. The pyrazolo derivative crystallises as solvate with 1.5 water molecules per quinoline molecule. In its crystal structure donor and acceptor functionalities form dimers, via hydrogen bonds, which are connected into an infinite pattern through hydrogen bonded water molecules.