Norfloxacin supplier | CasNO.70458-96-7

Name
Norfloxacin
EINECS 274-614-4
CAS No. 70458-96-7
Article Data28
CAS DataBase
Density 1.344 g/cm³
Solubility Soluble in acetic acid. Also soluble in acetone or cloroform. Slightly soluble in water
Melting Point 220 °C
Formula C₁₆H₁₈FN₃O₃
Boiling Point 555.8 °C at 760 mmHg
Molecular Weight 319.336
Flash Point 289.9 °C
Transport Information
Appearance Off-white to light yellow cryst powder
Safety 26-37/39
Risk Codes 20/21/22-36/37/38
Molecular Structure
Hazard Symbols Xn
Synonyms 1-Ethyl-6-fluoro-1,4-dihydro-7-(1-piperazinyl)-4-oxo-3-quinolinecarboxylicacid;AM 715;Amicrobin;Baccidal;Barazan;Barotham;Chibroxin;Chibroxine;Esclebin;Floxacin;Floxacin 400;Fulgram;Gonorcin;Lexinor;Mk 0366;N-Demethylpefloxacin;N-Desmethylpefloxacin;Neofloxacin;Neofloxin;Noflo;Nofocin;Nolicin;Noracin;Noraxin;Norbid;Norflox 400;
PSA 74.57000
LogP 1.66210

Synthetic route

: 94498-83-6
C16H17BF3N3O3

: 70458-96-7
1-ethyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-3-quinoline carboxylic acid

Conditions

Conditions	Yield
With sodium hydroxide Heating;	98%

: 110-85-0
piperazine

: 68077-26-9
7-chloro-1-ethyl-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

: 70458-96-7
1-ethyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-3-quinoline carboxylic acid

Conditions

Conditions	Yield
With aluminum tri-bromide In ethanol at 65℃; for 5h; Temperature; Solvent; Reagent/catalyst;	91.7%
In N,N-dimethyl-formamide at 100 - 130℃; for 2h;	82.9%
In ethanol at 120℃; for 0.583333h; Microwave irradiation;	80%
at 130 - 140℃; for 5h;	66%
In dimethyl sulfoxide at 140℃;

: 1-ethyl-6-fluoro-7-chloro-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid sodium salt

: 110-85-0
piperazine

: 70458-96-7
1-ethyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-3-quinoline carboxylic acid

Conditions

Conditions	Yield
With aluminum (III) chloride In i-Amyl alcohol at 140℃; for 8h; Solvent; Temperature;	90.9%

: 110-85-0
piperazine

: 68077-26-9
7-chloro-1-ethyl-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

A: 70458-96-7
1-ethyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-3-quinoline carboxylic acid

B: 75001-78-4
7-chloro-1-ethyl-1,4-dihydro-4-oxo-6-(1-piperazinyl)quinoline-3-carboxylic acid

Conditions

Conditions	Yield
In water for 16h; Heating;	A 85% B n/a
In water at 150℃; for 5h;	A 50% B n/a
In dimethylsulfoxide-d6 at 100℃; Rate constant;
In dimethylsulfoxide-d6 at 120 - 130℃;	A 80 % Spectr. B 20 % Spectr.

...Expand

: 74011-47-5
ethyl 1-ethyl-6-fluoro-4-oxo-7-(piperazin-1-yl)-1,4-dihydroquinoline-3-carboxylate

: 70458-96-7
1-ethyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-3-quinoline carboxylic acid

Conditions

Conditions	Yield
With hydrogenchloride In water; acetic acid	84%
With sodium hydroxide for 2h; Heating; Yield given;

: 110-85-0
piperazine

: 70032-25-6
6,7-difluoro-1-ethyl-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

: 70458-96-7
1-ethyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-3-quinoline carboxylic acid

Conditions

Conditions	Yield
With triethylamine In water for 8h; Reflux;	84%
With triethylamine In water for 5h; Substitution; Heating;	79%

: 99726-81-5
1-Ethyl-6-fluoro-1,4-dihydro-7-<4-(cyanomethyl)-1-piperazinyl>-4-oxoquinoline-3-carboxylic acid

: 70458-96-7
1-ethyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-3-quinoline carboxylic acid

Conditions

Conditions	Yield
With 3-chloro-benzenecarboperoxoic acid In chloroform at 50℃; for 10h;	83%

: 110-85-0
piperazine

: 106648-05-9
2-(2,4-Dichlor-5-fluorbenzoyl)-3-ethylaminoacrylsaeure-ethylester

: 70458-96-7
1-ethyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-3-quinoline carboxylic acid

Conditions

Conditions	Yield
Stage #1: 2-(2,4-Dichlor-5-fluorbenzoyl)-3-ethylaminoacrylsaeure-ethylester With sodium hydroxide In 5,5-dimethyl-1,3-cyclohexadiene at 125 - 130℃; Stage #2: piperazine With aluminum (III) chloride In ethanol at 85℃; for 8h; Reagent/catalyst; Temperature; Solvent;	77.3%

: 118476-20-3
1-Ethyl-6-fluoro-1,4-dihydro-7-<4-<(ethoxycarbonyl)methyl>-1-piperazinyl>-4-oxoquinoline-3-carboxylic Acid

: 70458-96-7
1-ethyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-3-quinoline carboxylic acid

Conditions

Conditions	Yield
With 3-chloro-benzenecarboperoxoic acid In chloroform at 50℃; for 10h;	77%
Multi-step reaction with 2 steps 1: 470 mg / m-chloroperbenzoic acid (MCPBA) / CHCl3 / 3 h / 0 °C 2: 239 mg / CHCl3 / 1) r.t., 5 min, 2) 50 deg C, 6 h View Scheme

: 110-85-0
piperazine

: 68077-26-9
7-chloro-1-ethyl-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

: 7440-44-0
pyrographite

: 70458-96-7
1-ethyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-3-quinoline carboxylic acid

Conditions

Conditions	Yield
With pyridine; sodium hydroxide In phosphorus pentaoxide; ethanol; water; acetic acid; N,N-dimethyl-formamide	70%

...Expand

: 110-85-0
piperazine

: 100505-08-6
1-ethyl-6,7-difluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid,ethyl ester

: 70458-96-7
1-ethyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-3-quinoline carboxylic acid

Conditions

Conditions	Yield
With triethylamine In water for 10h; Substitution; Heating;	69%

: 127142-90-9
7-{4-[(tert-butoxy)carbonyl]piperazin-1-yl}-1-ethyl-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

: 70458-96-7
1-ethyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-3-quinoline carboxylic acid

Conditions

Conditions	Yield
With trifluoroacetic acid In dichloromethane at 0 - 20℃; for 4h;	68.9%

: 103175-73-1
1-ethyl-6-fluoro-1,4-dihydro-4-oxo-7-[4-(2-oxopropyl)-1-piperazinyl]-quinoline-3-carboxylic acid

A: 70458-96-7
1-ethyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-3-quinoline carboxylic acid

B: 70459-04-0
1-ethyl-6-fluoro-7-(4-formylpiperazin-1-yl)-1,4-dihydro-4-oxoquinoline-3-carboxylic acid

Conditions

Conditions	Yield
With 3-chloro-benzenecarboperoxoic acid In chloroform for 6h; Ambient temperature;	A 59% B 32%
With 3-chloro-benzenecarboperoxoic acid In chloroform for 6h; Mechanism; Product distribution; Ambient temperature; other substrates;	A 59% B 32%

: 110-85-0
piperazine

: 70032-25-6
6,7-difluoro-1-ethyl-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

: 68-12-2, 33513-42-7
N,N-dimethyl-formamide

A: 70458-96-7
1-ethyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-3-quinoline carboxylic acid

B: 70459-04-0
1-ethyl-6-fluoro-7-(4-formylpiperazin-1-yl)-1,4-dihydro-4-oxoquinoline-3-carboxylic acid

Conditions

Conditions	Yield
Stage #1: piperazine; 6,7-difluoro-1-ethyl-4-oxo-1,4-dihydroquinoline-3-carboxylic acid With triethylamine In N,N-dimethyl-formamide for 10h; Substitution; Heating; Stage #2: N,N-dimethyl-formamide for 10h; Formylation; Heating;	A 55% B 32%

...Expand

: 103258-03-3
1-ethyl-6-fluoro-1,4-dihydro-7-<4-(1-methyl-2-oxopropyl)-1-piperazinyl>-4-oxoquinoline-3-carboxylic acid

A: 70458-96-7
1-ethyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-3-quinoline carboxylic acid

B: 70459-04-0
1-ethyl-6-fluoro-7-(4-formylpiperazin-1-yl)-1,4-dihydro-4-oxoquinoline-3-carboxylic acid

Conditions

Conditions	Yield
With 3-chloro-benzenecarboperoxoic acid In chloroform for 12h; Ambient temperature;	A 52% B 27%

: 1369320-98-8
1-ethyl-6-fluoro-4-oxo-7-piperazin-1-yl-1,4-dihydro-quinoline-3-carboxylic acid 2-hexadecanoyloxy-1-hexadecanoyloxymethyl-ethyl ester

: 70458-96-7
1-ethyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-3-quinoline carboxylic acid

Conditions

Conditions	Yield
With lipase at 37℃; for 10h; pH=1.2; Kinetics; Solvent; pH-value; Reagent/catalyst; aq. buffer; Enzymatic reaction;	32%

: 85195-76-2
N-<(5-Methyl-2-oxo-1,3-dioxol-4-yl)methyl>norfloxacin

A: 124-38-9
carbon dioxide

B: 70458-96-7
1-ethyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-3-quinoline carboxylic acid

C: 431-03-8
dimethylglyoxal

Conditions

Conditions	Yield
In potassium hydroxide for 0.166667h; Ambient temperature; hydrolyses (in AGJ :half-life 12 h; in AIJ :half-life 8.5 h); taken for complete hydrolysis in 40 percent mouse blood : 15 min;;

...Expand

: 105439-96-1
N-(2-oxo-1,3-dioxol-4-yl)methyl NFLX

A: 124-38-9
carbon dioxide

B: 70458-96-7
1-ethyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-3-quinoline carboxylic acid

C: 78-98-8
2-oxopropanal

Conditions

Conditions	Yield
In potassium hydroxide for 0.166667h; Ambient temperature; hydrolyses (in AGJ :half-life 0.7 h; in AIJ :half-life 1.5 h); taken for complete hydrolysis in 40 percent mouse blood : 10 min;;

...Expand

: 105439-98-3
N-(4-oxo-2-hexen-3-yloxy)carbonyl NFLX

A: 4437-51-8
3,4-hexanedione

B: 124-38-9
carbon dioxide

C: 70458-96-7
1-ethyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-3-quinoline carboxylic acid

Conditions

Conditions	Yield
In potassium hydroxide for 0.166667h; Ambient temperature; hydrolyses (in AGJ :half-life >20 h; in AIJ :half-life >20 h); taken for complete hydrolysis in 40 percent mouse blood : >200 min;;

...Expand

: 86761-10-6
N-(5-tert-butyl-2-oxo-1,3-dioxol-4-yl)methyl NFLX

A: 40898-19-9
4,4-dimethyl-2,3-pentanedione

B: 124-38-9
carbon dioxide

C: 70458-96-7
1-ethyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-3-quinoline carboxylic acid

Conditions

Conditions	Yield
In potassium hydroxide for 0.166667h; Ambient temperature; hydrolyses (in AGJ :half-life >20 h; in AIJ :half-life 18 h); taken for complete hydrolysis in 40 percent mouse blood : 120 min;;

...Expand

: 105439-97-2
N-(5-phenyl-2-oxo-1,3-dioxol-4-yl)methyl NFLX

A: 124-38-9
carbon dioxide

B: 70458-96-7
1-ethyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-3-quinoline carboxylic acid

C: 579-07-7
1-Phenylpropane-1,2-dione

Conditions

Conditions	Yield
In potassium hydroxide for 0.166667h; Ambient temperature; hydrolyses (in AGJ :half-life >20 h; in AIJ :half-life >20 h); taken for complete hydrolysis in 40 percent mouse blood : 150 min;;

...Expand

: 105440-03-7
N-(5-methyl-2-oxo-1,3-dioxol-4-yl)methyl NFLX (5-methyl-2-oxo-1,3-dioxol-4-yl)methyl ester

A: 40898-19-9
4,4-dimethyl-2,3-pentanedione

B: 124-38-9
carbon dioxide

C: 70458-96-7
1-ethyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-3-quinoline carboxylic acid

Conditions

Conditions	Yield
In potassium hydroxide for 0.166667h; Ambient temperature; hydrolyses (in AGJ :half-life 18 h; in AIJ :half-life 11 h); taken for complete hydrolysis in 40 percent mouse blood : 20 min;;

...Expand

: 1-Ethyl-6-fluoro-4-oxo-7-[4-(2-oxo-propyl)-4-oxy-piperazin-1-yl]-1,4-dihydro-quinoline-3-carboxylic acid

: 70458-96-7
1-ethyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-3-quinoline carboxylic acid

Conditions

Conditions	Yield
In chloroform Ambient temperature;

: 7-(4-Ethoxycarbonylmethyl-4-oxy-piperazin-1-yl)-1-ethyl-6-fluoro-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid

: 70458-96-7
1-ethyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-3-quinoline carboxylic acid

Conditions

Conditions	Yield
In chloroform 1) r.t., 5 min, 2) 50 deg C, 6 h;	239 mg

: 110-85-0
piperazine

: C16H14BClFNO7

: 70458-96-7
1-ethyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-3-quinoline carboxylic acid

Conditions

Conditions	Yield
With sodium hydroxide 1.) DMSO, 110 deg C, 2 h; 2.) reflux, 1 h; Yield given;

: 94498-82-5
C12H8BClF3NO3

A: 70458-96-7
1-ethyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-3-quinoline carboxylic acid

B p-methyl-ω-haloacetophenone: p-methyl-ω-haloacetophenone

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 98 percent / triethylamine / dimethylsulfoxide / 3 h / 60 °C 2: 98 percent / aq. NaOH / Heating View Scheme

: 68077-26-9
7-chloro-1-ethyl-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

A: 70458-96-7
1-ethyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-3-quinoline carboxylic acid

B p-methyl-ω-haloacetophenone: p-methyl-ω-haloacetophenone

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 95 percent / BF3*Et2O / diethyl ether; CH2Cl2 / Heating 2: 98 percent / triethylamine / dimethylsulfoxide / 3 h / 60 °C 3: 98 percent / aq. NaOH / Heating View Scheme

: 367-21-5
3-chloro-4-fluorophenylamine

: 70458-96-7
1-ethyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-3-quinoline carboxylic acid

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1: 100 percent / 2 h / 120 - 130 °C 2: diphenyl ether / 1 h / Heating 3: 90 percent / K2CO3 / dimethylformamide / 10 h / 80 - 90 °C 4: 90 percent / 2N NaOH / 2 h / Heating 5: 66 percent / 5 h / 130 - 140 °C View Scheme

: 70458-94-5
1-ethyl-6-fluoro-7-chloro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid ethyl ester

: 70458-96-7
1-ethyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-3-quinoline carboxylic acid

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 90 percent / 2N NaOH / 2 h / Heating 2: 66 percent / 5 h / 130 - 140 °C View Scheme
Multi-step reaction with 2 steps 1: hydrogenchloride / methanol; water / 2 h / Reflux 2: N,N-dimethyl-formamide / 2 h / 100 - 130 °C View Scheme
Multi-step reaction with 2 steps 1: sodium hydroxide; water / ethanol / 2.5 h / Reflux 2: dimethyl sulfoxide / 140 °C View Scheme

: 1416579-55-9
N-(4-(2-chloroacetamido)butyl)-2,3-diisopropoxybenzamide

: 70458-96-7
1-ethyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-3-quinoline carboxylic acid

: 1416579-56-0
C35H46FN5O7

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine; potassium iodide In N,N-dimethyl-formamide at 20℃; for 36h;	100%

: 50-00-0
formaldehyd

: 5-{[4-(2-methoxyphenyl)piperazin-1-yl]methyl}-4-benzyl-4H-1,2,4-triazole-3-thiol

: 70458-96-7
1-ethyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-3-quinoline carboxylic acid

: C38H43FN8O4S

Conditions

Conditions	Yield
In N,N-dimethyl-formamide at 100℃; for 0.1h; Temperature; Time; Mannich Aminomethylation; Microwave irradiation; Sealed tube;	100%

...Expand

: 3001-72-7
DBN

: 70458-96-7
1-ethyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-3-quinoline carboxylic acid

: C16H18FN3O3*C7H12N2

Conditions

Conditions	Yield
In methanol; water at 20℃; for 2h;	100%

: C57H55N5O10

: 70458-96-7
1-ethyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-3-quinoline carboxylic acid

: C67H68FN7O10

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide	99%

: 105-36-2
ethyl bromoacetate

: 70458-96-7
1-ethyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-3-quinoline carboxylic acid

: 118476-20-3
1-Ethyl-6-fluoro-1,4-dihydro-7-<4-<(ethoxycarbonyl)methyl>-1-piperazinyl>-4-oxoquinoline-3-carboxylic Acid

Conditions

Conditions	Yield
Stage #1: 1-ethyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-3-quinoline carboxylic acid With sodium ethanolate In ethanol for 0.0666667h; Microwave irradiation; Stage #2: ethyl bromoacetate for 0.25h; Reagent/catalyst; Time; Microwave irradiation;	98%
With potassium hydrogencarbonate In N,N-dimethyl-formamide at 20℃;	74%
With potassium hydrogencarbonate In N,N-dimethyl-formamide for 8h; Ambient temperature;	61%

: 70458-96-7
1-ethyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-3-quinoline carboxylic acid

A: 50-00-0
formaldehyd

B: 7664-41-7
ammonia

C: 75001-63-7
6-fluoro-7-amino-1-ethyl-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid

Conditions

Conditions	Yield
With potassium permanganate; cetyltrimethylammonim bromide; acetic acid In water; acetonitrile at 24.84℃; Kinetics; Catalytic behavior; Mechanism; Thermodynamic data; Activation energy; Temperature; Concentration; Solvent; UV-irradiation;	A n/a B n/a C 98%

...Expand

: 3-(4-benzyl-5-oxo-4,5-dihydro-1H-1,2,4-triazol-3-yl)-1-ethyl-7-methyl-1,8-naphthyridin-4(1H)-one

: 70458-96-7
1-ethyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-3-quinoline carboxylic acid

: 6-(4-{[4-benzyl-3-(1-ethyl-7-methyl-4-oxo-1,4-dihydro-1,8-naphthyridin-3-yl)-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl]methyl}piperazin-1-yl)-1-ethyl-5-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

Conditions

Conditions	Yield
With formaldehyd In dimethyl sulfoxide at 50℃; Microwave irradiation;	98%

: 50-00-0
formaldehyd

: 3-(4-benzyl-5-thioxo-4,5-dihydro-1H-1,2,4-triazol-3-yl)-1-ethyl-7-methyl-1,8-naphthyridin-4(1H)-one

: 70458-96-7
1-ethyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-3-quinoline carboxylic acid

: 6-(4-{[4-benzyl-3-(1-ethyl-7-methyl-4-oxo-1,4-dihydro-1,8-naphthyridin-3-yl)-5-thioxo-4,5-dihydro-1H-1,2,4-triazol-1-yl]methyl}piperazin-1-yl)-1-ethyl-5-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

Conditions

Conditions	Yield
In dimethyl sulfoxide at 50℃; for 0.0833333h; Temperature; Microwave irradiation;	98%

...Expand

: 50-00-0
formaldehyd

: 1-ethyl-3-(4-ethyl-5-thioxo-4,5-dihydro-1H-1,2,4-triazol-3-yl)-7-methyl-1,8-naphthyridin-4(1H)-one

: 70458-96-7
1-ethyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-3-quinoline carboxylic acid

: 1-ethyl-6-(4-{[4-ethyl-3-(1-ethyl-7-methyl-4-oxo-1,4-dihydro-1,8-naphthyridin-3-yl)-5-thioxo-4,5-dihydro-1H-1,2,4-triazol-1-yl]methyl}piperazin-1-yl)-5-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

Conditions

Conditions	Yield
Stage #1: formaldehyd; 1-ethyl-3-(4-ethyl-5-thioxo-4,5-dihydro-1H-1,2,4-triazol-3-yl)-7-methyl-1,8-naphthyridin-4(1H)-one; 1-ethyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-3-quinoline carboxylic acid In dimethyl sulfoxide at 20℃; for 0.25h; Stage #2: With indium(III) chloride In dimethyl sulfoxide for 5h; Temperature;	98%

...Expand

: 50-00-0
formaldehyd

: 1456620-74-8
{[4-(2-methoxyphenyl)piperazin-1-yl]methyl}-1,3,4-oxadiazole-2-thiol

: 70458-96-7
1-ethyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-3-quinoline carboxylic acid

: 1-ethyl-6-fluoro-7-(4-{[5-{[4-(2-methoxyphenyl)piperazin-1-yl]methyl}-2-thioxo-1,3,4-oxadiazole-3(2H)-yl]methyl}piperazin-1-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

Conditions

Conditions	Yield
In N,N-dimethyl-formamide at 100℃; for 0.0833333h; Temperature; Time; Mannich Aminomethylation; Microwave irradiation; Sealed tube;	98%

...Expand

: 14625-39-9
2-(chloromethyl)-5-nitro-1H-benzo[d]imidazole

: 70458-96-7
1-ethyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-3-quinoline carboxylic acid

: 1-ethyl-6-fluoro-1,4-dihydro-7-(4-((5-nitro-1H-benzo[d]imidazol-2-yl)methyl)piperazin-1-yl)-4-oxoquinoline-3-carboxylic acid

Conditions

Conditions	Yield
With sodium hydrogencarbonate In N,N-dimethyl-formamide at 20℃; for 72h;	98%

: 4-chloro-6-[1-(vinylsulfonyl)pyrrolidin-2-yl]benzene-1,3-diol

: 70458-96-7
1-ethyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-3-quinoline carboxylic acid

: C28H32ClFN4O7S

Conditions

Conditions	Yield
With triethylamine In ethanol; water Michael Addition; Reflux;	98%

: 71831-21-5
4-(bromomethyl)benzyl alcohol

: 70458-96-7
1-ethyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-3-quinoline carboxylic acid

: 1-ethyl-6-fluoro-7-(4-(4-(hydroxymethyl)benzyl)piperazin-1-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

Conditions

Conditions	Yield
Stage #1: 1-ethyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-3-quinoline carboxylic acid With potassium carbonate In water; acetonitrile at 20℃; for 0.0833333h; Stage #2: 4-(bromomethyl)benzyl alcohol In water; acetonitrile at 20℃;	97.1%

: 108-24-7
acetic anhydride

: 70458-96-7
1-ethyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-3-quinoline carboxylic acid

: 74011-56-6
7-(4-acetyl-1-piperazinyl)-1-ethyl-6-fluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid

Conditions

Conditions	Yield
With triethylamine at 90 - 100℃;	97%
With acetic acid at 35℃; for 1h;	69%
for 5h; Heating;
With acetic acid at 35℃; for 1h;

: 50-00-0
formaldehyd

: 5-{[(3-fluoro-4-thiomorpholin-4-ylphenyl)amino]methyl}-4-phenyl-4H-1,2,4-triazole-3-thiol

: 70458-96-7
1-ethyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-3-quinoline carboxylic acid

: 1-ethyl-6-fluoro-7-{4-[(3-{[(3-fluoro-4-thiomorpholin-4-ylphenyl)amino]methyl}-4-phenyl-5-thioxo-4,5-dihydro-1H-1,2,4-triazol-1-yl)methyl]piperazin-1-yl}-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

Conditions

Conditions	Yield
With hydrogenchloride In neat (no solvent) for 0.0833333h; Solvent; Time; Reagent/catalyst; Mannich Aminomethylation; Microwave irradiation; Sealed tube; Green chemistry;	97%

...Expand

: 50-00-0
formaldehyd

: 5-[({3-fluoro-4-[4-(4-fluorophenyl)piperazin-1-yl]phenyl}amino)methyl]-1,3,4-oxadiazole-2(3H)-thione

: 70458-96-7
1-ethyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-3-quinoline carboxylic acid

: 1-ethyl-6-fluoro-7-(4-{[5-[({3-fluoro-4-[4-(4-fluorophenyl)piperazin-1-yl]phenyl}amino)methyl]-2-thioxo-1,3,4-oxadiazol-3(2H)-yl]methyl}piperazin-1-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

Conditions

Conditions	Yield
With hydrogenchloride In neat (no solvent) at 50℃; for 0.333333h; Reagent/catalyst; Solvent; Time; Microwave irradiation; Sealed tube;	97%

...Expand

: 50-00-0
formaldehyd

: 5-{[4-(4-nitrophenyl)piperazin-1-yl]methyl}-4-ethyl-4H-1,2,4-triazole-3-thiol

: 70458-96-7
1-ethyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-3-quinoline carboxylic acid

: 1-ethyl-6-fluoro-7-{4-[(3-{[4-(4-nitrophenyl)piperazin-1-yl]methyl}-4-ethyl-5-thioxo-4,5-dihydro-1H-1,2,4-triazole-1-yl)methyl]piperazin-1-yl}-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

Conditions

Conditions	Yield
In neat (no solvent) for 0.25h; Solvent; Mannich Aminomethylation; Microwave irradiation; Green chemistry;	97%

...Expand

: 50-00-0
formaldehyd

: 91-56-5
indole-2,3-dione

: 70458-96-7
1-ethyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-3-quinoline carboxylic acid

: 7-[4-(2,3-dioxo-2,3-dihydro-indol-1-ylmethyl)-piperazin-1-yl]-1-ethyl-6-fluoro-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid

Conditions

Conditions	Yield
With acetic acid In water for 2h; Mannich reaction; Heating;	96%

...Expand

: 176720-62-0
3-(bromoacetyl)coumarin oxime

: 70458-96-7
1-ethyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-3-quinoline carboxylic acid

: C27H25FN4O6

Conditions

Conditions	Yield
With sodium hydrogencarbonate In N,N-dimethyl-formamide at 22 - 25℃; for 12h;	96%

: 50-00-0
formaldehyd

: 5-{[4-(4-nitrophenyl)piperazin-1-yl]methyl}-4-benzyl-4H-1,2,4-triazole-3-one

: 70458-96-7
1-ethyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-3-quinoline carboxylic acid

: 1-ethyl-6-fluoro-7-{4-[(3-{[4-(4-nitrophenyl)piperazin-1-yl]methyl}-4-benzyl-5-oxo-4,5-dihydro-1H-1,2,4-triazole-1-yl)methyl]piperazin-1-yl}-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

Conditions

Conditions	Yield
In neat (no solvent) for 0.25h; Solvent; Mannich Aminomethylation; Microwave irradiation; Green chemistry;	96%

...Expand

: 50-00-0
formaldehyd

: 4-(4-fluorophenyl)-5-[(4-phenylpiperazin-1-yl)methyl]-4H-1,2,4-triazol-3-thiol

: 70458-96-7
1-ethyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-3-quinoline carboxylic acid

: 1-ethyl-6-fluoro-4-oxo-7-[4-({4-fluorophenyl-3-[(4-phenylpiperazin-1-yl)methyl]-5-thioxo-4,5-dihydro-1H-1,2,4-triazol-1-yl}methyl)piperazin-1-yl]-1,4-dihydroquinolin-3-carboxylic acid

Conditions

Conditions	Yield
In N,N-dimethyl-formamide for 0.333333h; Mannich Aminomethylation; Microwave irradiation; Sealed tube;	96%

...Expand

: 50-00-0
formaldehyd

: 87-48-9
5-Bromo-1H-indole-2,3-dione

: 70458-96-7
1-ethyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-3-quinoline carboxylic acid

: 7-[4-(5-bromo-2,3-dioxo-2,3-dihydro-indol-1-ylmethyl)-piperazin-1-yl]-1-ethyl-6-fluoro-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid

Conditions

Conditions	Yield
With acetic acid In water for 2h; Mannich reaction; Heating;	95.14%

...Expand

: 70458-96-7
1-ethyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-3-quinoline carboxylic acid

: 68-12-2, 33513-42-7
N,N-dimethyl-formamide

: 959774-07-3
7-(4-formylpiperazin-1-yl)-1-ethyl-6-fluoroquinoline-4-one

Conditions

Conditions	Yield
With potassium cyanide at 120℃; for 24h;	95%

: 5195-29-9
4-bromophenylglyoxal

: 70458-96-7
1-ethyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-3-quinoline carboxylic acid

: 7-(4-(2-(4-bromophenyl)-2-oxoethanethioyl)piperazin-1-yl)-1-ethyl-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

Conditions

Conditions	Yield
With sulfur; sodium sulfide In N,N-dimethyl-formamide at 110℃; for 7h; Willgerodt-Kindler Rearrangement;	95%

: 70458-96-7
1-ethyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-3-quinoline carboxylic acid

: 80-70-6
N,N,N',N'-tetramethylguanidine

: C16H18FN3O3*C5H13N3

Conditions

Conditions	Yield
In methanol at 20℃; for 3h;	95%

: 70458-96-7
1-ethyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-3-quinoline carboxylic acid

: 68077-27-0
Norfloxacin hydrochloride

Conditions

Conditions	Yield
With hydrogenchloride In 1,4-dioxane; dichloromethane at 20℃; for 1h;	95%
Multi-step reaction with 2 steps 1: sodium hydroxide / tetrahydrofuran / 20 °C 2: hydrogenchloride / ethanol; water / 3 h / Reflux View Scheme

: 50-00-0
formaldehyd

: 4-ethyl-5-[(4-phenylpiperazin-1-yl)methyl]-4H-1,2,4-triazol-3-thiol

: 70458-96-7
1-ethyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-3-quinoline carboxylic acid

: 1-ethyl-6-fluoro-4-oxo-7-[4-({4-ethyl-3-[(4-phenylpiperazin-1-yl)methyl]-5-thioxo-4,5-dihydro-1H-1,2,4-triazol-1-yl}methyl)piperazin-1-yl]-1,4-dihydroquinolin-3-carboxylic acid

Conditions

Conditions	Yield
In N,N-dimethyl-formamide for 0.333333h; Mannich Aminomethylation; Microwave irradiation; Sealed tube;	95%

...Expand

: 24424-99-5
di-tert-butyl dicarbonate

: 70458-96-7
1-ethyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-3-quinoline carboxylic acid

: 127142-90-9
7-{4-[(tert-butoxy)carbonyl]piperazin-1-yl}-1-ethyl-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

Conditions

Conditions	Yield
With sodium hydroxide In tetrahydrofuran; water at 20℃;	94.2%
With triethylamine In dichloromethane at 20℃; for 2.5h;
With sodium hydroxide In tetrahydrofuran at 20℃;	126 mg

: 4974-57-6
4-nitrophenylglyoxal

: 70458-96-7
1-ethyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-3-quinoline carboxylic acid

: 1-ethyl-6-fluoro-7-(4-(2-(4-nitrophenyl)-2-oxoethanethioyl)piperazin-1-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

Conditions

Conditions	Yield
With sulfur; sodium sulfide In N,N-dimethyl-formamide at 110℃; for 7h; Willgerodt-Kindler Rearrangement;	94%

Norfloxacin Chemical Properties

IUPAC Name: 1-Ethyl-6-fluoro-4-oxo-7-piperazin-1-ylquinoline-3-carboxylic acid
Synonyms of Norfloxacin (CAS NO.70458-96-7): 1,4-Dihydro-1-ethyl-6-fluoro-4-oxo-7-(1-piperazinyl)-3-quinolinecarboxylic acid ;1-Ethyl-6-fluor-1,4-dihydro-4-oxo-7-(1-piperazinyl)-3-chinolincarbonsaeure ; Baccidal ; Barazan ; Norfloxacin ; Norfloxacinum ; 3-Quinolinecarboxylic acid, 1,4-dihydro-1-ethyl-6-fluoro-4-oxo-7-(1-piperazinyl)-
CAS NO: 70458-96-7
Molecular Formula: C₁₆H₁₈FN₃O₃
Molecular Weight: 319.33
Molecular Structure:
EINECS: 274-614-4
H bond acceptors: 6
H bond donors: 2
Freely Rotating Bonds: 3
Polar Surface Area: 53.09 Å2
Index of Refraction: 1.595
Molar Refractivity: 80.7 cm³
Molar Volume: 237.4 cm³
Surface Tension: 53.1 dyne/cm
Density: 1.344 g/cm³
Flash Point: 289.9 °C
Enthalpy of Vaporization: 88.09 kJ/mol
Boiling Point: 555.8 °C at 760 mmHg
Vapour Pressure: 3.45E-13 mmHg at 25°C
Melting Point: 220°C
Storage temp: 2-8°C
Appearance: Off-white to light yellow cryst powder
SMILES: O=C(O)\C2=C\N(c1cc(c(F)cc1C2=O)N3CCNCC3)CC
InChI: InChI=1/C16H18FN3O3/c1-2-19-9-11(16(22)23)15(21)10-7-12(17)14(8-13(10)19)20-5-3-18-4-6-20/h7-9,18H,2-6H2,1H3,(H,22,23)
InChIKey: OGJPXUAPXNRGGI-UHFFFAOYAC
Std. InChI: InChI=1S/C16H18FN3O3/c1-2-19-9-11(16(22)23)15(21)10-7-12(17)14(8-13(10)19)20-5-3-18-4-6-20/h7-9,18H,2-6H2,1H3,(H,22,23)
Std. InChIKey: OGJPXUAPXNRGGI-UHFFFAOYSA-N
Product Categories of Norfloxacin (CAS NO.70458-96-7): Pharmaceutical;Active Pharmaceutical Ingredients;APIs;Intermediates & Fine Chemicals;Pharmaceuticals;API's

Norfloxacin History

Uses of Norfloxacin has been licensed are quite limited as norfloxacin is to be considered a drug of last resort when all other antibiotics have failed. There are currently only three approved uses in the adult population and the other ineffective due to bacterial resistance. And, Norfloxacin interacts with a number of other drugs, as well as a number of herbal and natural supplements. Such interactions increase the risk of anticoagulation and the formation of non-absorbable complexes, as well as increasing the risk of toxicity.

Norfloxacin Uses

Norfloxacin (CAS NO.70458-96-7) is limited to the treatment of proven bacterial infections as following: Complicated urinary tract infections (restricted use); Uncomplicated urethral and cervical gonorrhea (however this indication is no longer considered to be effective by some experts due to bacterial resistance) ; Prostatitis due to Escherichia coli ; Syphilis treatment: Norfloxacin has not been shown to be effective in the treatment of syphilis.

Norfloxacin Toxicity Data With Reference

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
mammal (species unspecified)	LD50	oral	> 4gm/kg (4000mg/kg)		Journal of Medicinal Chemistry. Vol. 32, Pg. 671, 1989.
man	TDLo	oral	94mg/kg/13D-I (94mg/kg)	MUSCULOSKELETAL: OTHER CHANGES	New Zealand Medical Journal. Vol. 96, Pg. 590, 1983.
mouse	LD50	intramuscular	470mg/kg (470mg/kg)	BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)	Chemotherapy Vol. 29(Suppl,
mouse	LD50	intraperitoneal	1064mg/kg (1064mg/kg)		Ensho. Japanese Journal of Inflammation. Vol. 11, Pg. 343, 1991.
mouse	LD50	intravenous	220mg/kg (220mg/kg)	BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD	Chemotherapy Vol. 29(Suppl,
mouse	LD50	oral	4gm/kg (4000mg/kg)		Journal of Medicinal Chemistry. Vol. 30, Pg. 2163, 1987.
mouse	LD50	subcutaneous	> 1500mg/kg (1500mg/kg)		Yakkyoku. Pharmacy. Vol. 35, Pg. 1625, 1984.
rat	LD50	intramuscular	> 500mg/kg (500mg/kg)	BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES	Chemotherapy Vol. 29(Suppl,
rat	LD50	intravenous	245mg/kg (245mg/kg)	BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD	Chemotherapy Vol. 29(Suppl,
rat	LD50	oral	> 4gm/kg (4000mg/kg)		Yakkyoku. Pharmacy. Vol. 35, Pg. 1625, 1984.
rat	LD50	subcutaneous	> 1500mg/kg (1500mg/kg)		Yakkyoku. Pharmacy. Vol. 35, Pg. 1625, 1984.
women	TDLo	oral	48mg/kg/2D-I (48mg/kg)	BEHAVIORAL: MUSCLE WEAKNESS LIVER: "HEPATITIS (HEPATOCELLULAR NECROSIS), ZONAL" LIVER: LIVER FUNCTION TESTS IMPAIRED	Medical Journal of Australia. Vol. 159, Pg. 423, 1993.
women	TDLo	oral	48mg/kg/2D-I (48mg/kg)	LIVER: "HEPATITIS (HEPATOCELLULAR NECROSIS), ZONAL" BEHAVIORAL: MUSCLE WEAKNESS MUSCULOSKELETAL: JOINTS	Medical Journal of Australia. Vol. 159, Pg. 423, 1993.

Norfloxacin Safety Profile

Hazard Codes: Harmful Xn
Risk Statements: 20/21/22-36/37/38
R20/21/22: Harmful by inhalation, in contact with skin and if swallowed.
R36/37/38: Irritating to eyes, respiratory system and skin.
Safety Statements: 26-37/39
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S37/39: Wear suitable gloves and eye/face protection.
WGK Germany: 2
RTECS: VB2005000

Norfloxacin Specification

Overdose of Norfloxacin (CAS NO.70458-96-7):
Treatment of overdose include emptying of the stomach via induced vomiting or by gastric lavage. In addition Careful monitoring and supportive treatment, monitoring of renal and liver function, and maintaining adequate hydration is recommended by the manufacturer. Administration of magnesium, aluminum, or calcium containing antacids can reduce the absorption of norfloxacin.

Product Name

Norfloxacin

Synthetic route

Norfloxacin Chemical Properties

Norfloxacin History

Norfloxacin Uses

Norfloxacin Toxicity Data With Reference

Norfloxacin Safety Profile

Norfloxacin Specification

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