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42835-25-6

Basic Information
CAS No.: 42835-25-6
Name: Flumequine
Molecular Structure:
Molecular Structure of 42835-25-6 (Flumequine)
Formula: C14H12FNO3
Molecular Weight: 261.25
Synonyms: Apurone;Fantacin;Firestop;Flumigal;Flumiquil;Flumisol;Flumix;Imequyl;R 802;R 802 (bactericide);lumequine;1H,5H-Benzo[ij]quinolizine-2-carboxylicacid, 9-fluoro-6,7-dihydro-5-methyl-1-oxo-;
EINECS: 255-962-6
Density: 1.45 g/cm3
Melting Point: 253- 255 °C
Boiling Point: 439.7 °C at 760 mmHg
Flash Point: 219.7 °C
Solubility:
Appearance: white to off-white powder
Hazard Symbols: IrritantXi
Risk Codes: 36/37/38
Safety: 22-24/25-36/37/39-27-26
Transport Information:
PSA: 59.30000
LogP: 2.34600
Synthetic route
42835-47-2

9-fluoro-5-methyl-1-oxo-6,7-dihydro-1H,5H-pyrido[3,2,1-ij]quinoline-2-carboxylic acid ethyl ester

42835-25-6

flumequine

Conditions
ConditionsYield
With water at 100℃; for 3h;70.8%
With sodium hydroxide at 80℃; for 2h;304.5 mg
42835-89-2

6-fluoro-1,2,3,4-tetrahydro-2-methylquinoline

42835-25-6

flumequine

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 97 percent / 2.5 h / 125 °C
2: 69.1 percent / polyphosphoric acid / toluene / 6 h / 110 °C
3: 70.8 percent / H2O / 3 h / 100 °C
View Scheme
Multi-step reaction with 3 steps
1: 2.5 h / 125 °C
2: polyphosphoricacid / water / Heating
3: sodium hydroxide / 2 h / 80 °C
View Scheme
105450-09-7

Diethyl (2-methyl-6-fluorotetrahydro-quinolin-1-yl)methylenemalonate

42835-25-6

flumequine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 69.1 percent / polyphosphoric acid / toluene / 6 h / 110 °C
2: 70.8 percent / H2O / 3 h / 100 °C
View Scheme
42835-89-2

6-fluoro-1,2,3,4-tetrahydro-2-methylquinoline

87-13-8

diethyl 2-ethoxymethylenemalonate

42835-25-6

flumequine

Conditions
ConditionsYield
With PPA In water; toluene
In sodium hydroxide; toluene
With PPA In water; toluene
In sodium hydroxide; toluene
15568-85-1

5-methoxymethylene-2,2-dimethyl-1,3-dioxane-4,6-dione

42835-89-2

6-fluoro-1,2,3,4-tetrahydro-2-methylquinoline

A

123400-74-8

5-[1-(6-fluoro-2-methyl-1,2,3,4-tetrahydroquinolyl)]-methylene-2,2-dimethyl-1,3-dioxan-4,6-dione

B

42835-25-6

flumequine

Conditions
ConditionsYield
In tetrahydrofuran
123400-74-8

5-[1-(6-fluoro-2-methyl-1,2,3,4-tetrahydroquinolyl)]-methylene-2,2-dimethyl-1,3-dioxan-4,6-dione

42835-25-6

flumequine

Conditions
ConditionsYield
With sodium hydroxide; PPA In 5,5-dimethyl-1,3-cyclohexadiene
1128-61-6

6-fluoro-2-methyl-quinoline

42835-25-6

flumequine

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: hydrogen / toluene / 24 h / 120 °C / 3750.38 Torr / Autoclave
2: 2.5 h / 125 °C
3: polyphosphoricacid / water / Heating
4: sodium hydroxide / 2 h / 80 °C
View Scheme
95-14-7

1,2,3-Benzotriazole

42835-25-6

flumequine

1173208-75-7

2-(1H-benzo[d][1,2,3]triazole-1-carbonyl)-9-fluoro-5-methyl-6,7-dihydropyrido[3,2,1-ij]quinolin-1(5H)-one

Conditions
ConditionsYield
Stage #1: 1,2,3-Benzotriazole With thionyl chloride In dichloromethane at 25℃; for 0.5h;
Stage #2: flumequine In dichloromethane at 25℃; for 2h;
90%
42835-25-6

flumequine

7646-85-7

zinc(II) chloride

1268236-43-6

[Zn(flmq)2(H2O)2]

Conditions
ConditionsYield
Stage #1: flumequine With potassium hydroxide In methanol for 0.333333h;
Stage #2: zinc(II) chloride In methanol for 0.5h;
75%
1202-34-2

di(pyridin-2-yl)amine

cobalt(II) chloride hexahydrate

42835-25-6

flumequine

C38H31CoF2N5O6*H2O

Conditions
ConditionsYield
Stage #1: flumequine With potassium hydroxide In methanol for 0.5h;
Stage #2: di(pyridin-2-yl)amine; cobalt(II) chloride hexahydrate In methanol for 0.5h;
70%
42835-25-6

flumequine

9-fluoro-5-methyl-1-oxo-6,7-dihydro-1H,5H-pyrido[3,2,1-ij]quinoline-2-carbonitrile

Conditions
ConditionsYield
Stage #1: flumequine With polyphosphate ester; ammonia In chloroform at 119 - 123℃; for 45h;
Stage #2: With polyphosphate ester at 120℃; for 1.5h;
65%
366-18-7

[2,2]bipyridinyl

42835-25-6

flumequine

7646-85-7

zinc(II) chloride

[(2,2'-bipyridine)chlorido(flumequinato-k2O,O')zinc(II)]

Conditions
ConditionsYield
Stage #1: flumequine With potassium hydroxide In methanol for 0.333333h;
Stage #2: [2,2]bipyridinyl; zinc(II) chloride In methanol for 1h;
65%
67-56-1

methanol

66-71-7

1,10-Phenanthroline

42835-25-6

flumequine

7646-85-7

zinc(II) chloride

[Zn(flmq)(phen)Cl]*0.5MeOH

Conditions
ConditionsYield
Stage #1: flumequine With potassium hydroxide In methanol at 20℃; for 0.333333h;
Stage #2: methanol; 1,10-Phenanthroline; zinc(II) chloride
65%
366-18-7

[2,2]bipyridinyl

cobalt(II) chloride hexahydrate

42835-25-6

flumequine

C38H30CoF2N4O6*H2O

Conditions
ConditionsYield
Stage #1: flumequine With potassium hydroxide In methanol for 0.5h;
Stage #2: [2,2]bipyridinyl; cobalt(II) chloride hexahydrate In methanol for 0.5h;
65%
67-56-1

methanol

66-71-7

1,10-Phenanthroline

manganese(II) chloride tetrahydrate

42835-25-6

flumequine

[Mn(flmq)2(1,10-phenanthroline)]*2MeOH

Conditions
ConditionsYield
Stage #1: methanol; flumequine With potassium hydroxide for 0.5h;
Stage #2: 1,10-Phenanthroline; manganese(II) chloride tetrahydrate for 0.25h;
65%

zinc nitrate tetrahydrate

42835-25-6

flumequine

1268154-95-5

[Zn(II)(7-fluoro-12-methyl-4-oxo-1-azatricyclo[7.3.1.0(5,13)]trideca-2,5,7,9(13)-tetraene-3-carboxylate)2(H2O)2]*H2O

Conditions
ConditionsYield
With KOH In ethanol; water soln. of Zn salt in distd. H2O added dropwise to soln. of basified (KOH)flumequine in EtOH-H2O; stirred at room temp. overnight; ppt. isolated after filtration; elem. anal.;64%
366-18-7

[2,2]bipyridinyl

42835-25-6

flumequine

potassium hydroxide

7646-85-7

zinc(II) chloride

[(2,2'-bipyridine)di(9-fluoro-5-methyl-1-oxo-1,5,6,7-tetrahydropyrido[3,2,1-ij]quinoline-2-carboxylato-k2O,O')zinc(II)] dihydrate

Conditions
ConditionsYield
Stage #1: flumequine; potassium hydroxide In methanol
Stage #2: [2,2]bipyridinyl; zinc(II) chloride In methanol for 1h;
60%
67-56-1

methanol

66-71-7

1,10-Phenanthroline

42835-25-6

flumequine

7646-85-7

zinc(II) chloride

[Zn(flmq)2(phen)]*2MeOH

Conditions
ConditionsYield
With potassium hydroxide60%
66-71-7

1,10-Phenanthroline

cobalt(II) chloride hexahydrate

42835-25-6

flumequine

C40H30CoF2N4O6*1.6CH4O*0.4H2O

Conditions
ConditionsYield
Stage #1: flumequine With potassium hydroxide In methanol for 0.5h;
Stage #2: 1,10-Phenanthroline; cobalt(II) chloride hexahydrate In methanol for 0.5h;
60%
67-56-1

methanol

cobalt(II) chloride hexahydrate

42835-25-6

flumequine

Co(2+)*2CH4O*2C14H11FNO3(1-)

Conditions
ConditionsYield
Stage #1: methanol; flumequine With potassium hydroxide for 0.5h;
Stage #2: cobalt(II) chloride hexahydrate In methanol
60%
67-56-1

methanol

manganese(II) chloride tetrahydrate

42835-25-6

flumequine

C30H30F2MnN2O8

Conditions
ConditionsYield
Stage #1: methanol; flumequine With potassium hydroxide for 0.5h;
Stage #2: manganese(II) chloride tetrahydrate for 0.5h;
60%
1202-34-2

di(pyridin-2-yl)amine

manganese(II) chloride tetrahydrate

42835-25-6

flumequine

Mn(flmq)2(2,2′-bipyridylamine)

Conditions
ConditionsYield
Stage #1: flumequine With potassium hydroxide In methanol for 0.5h;
Stage #2: di(pyridin-2-yl)amine; manganese(II) chloride tetrahydrate In methanol for 0.25h;
60%

copper(II) nitrate trihydrate

42835-25-6

flumequine

1268154-93-3

Cu(II)(7-fluoro-12-methyl-4-oxo-1-azatricyclo[7.3.1.0(5,13)]trideca-2,5,7,9(13)-tetraene-3-carboxylate)2(H2O)2

Conditions
ConditionsYield
With KOH In ethanol; water soln. of Cu salt in distd. H2O added dropwise to soln. of basified (KOH)flumequine in EtOH-H2O; stirred at room temp. for 2 h; solvent removed; washed with distd. H2O and EtOH; dried under vac.; elem. anal.;51%

zinc acetate hydrate

100-21-0

terephthalic acid

42835-25-6

flumequine

[Zn2(flmq)2(bdc)(H2O)2]

Conditions
ConditionsYield
With potassium hydroxide at 150℃; for 72h; Autoclave; High pressure;48%
57933-83-2

Isopropenyl chloroformate

42835-25-6

flumequine

C18H16FNO5

Conditions
ConditionsYield
With triethylamine In dichloromethane
42835-25-6

flumequine

9-fluoro-6,7-dihydro-5-methyl-N-[2-(4-pyridyl)ethyl]-1-oxo-1H,5H-benzo-[i,j]quinolizine-2-carboxamide

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: Et3N / CH2Cl2
View Scheme
64-18-6

formic acid

42835-25-6

flumequine

887262-12-6

9-({2-[(2-hydroxyethyl)oxy]ethyl}amino)-5-methyl-1-oxo-6,7-dihydro-1H,5H-pyrido[3,2,1-ij]quinoline-2-carboxylic acid formate

Conditions
ConditionsYield
Stage #1: flumequine; 2-(2-Aminoethoxy)ethanol In 1-methyl-pyrrolidin-2-one at 220℃; for 1h; Microwave irradiation;
Stage #2: formic acid In water; acetonitrile
64-18-6

formic acid

42835-25-6

flumequine

887262-13-7

9-({2-[(2-aminoethyl)oxy]ethyl}amino)-5-methyl-1-oxo-6,7-dihydro-1H,5H-pyrido[3,2,1-ij]quinoline-2-carboxylic acid formate

Conditions
ConditionsYield
Stage #1: 2,2'-diaminodiethyl ether; flumequine In 1-methyl-pyrrolidin-2-one at 200℃; for 1h; Microwave irradiation;
Stage #2: formic acid In water; acetonitrile
64-18-6

formic acid

42835-25-6

flumequine

887262-24-0

9-[(2-aminoethyl)amino]-5-methyl-1-oxo-6,7-dihydro-1H,5H-pyrido[3,2,1-ij]quinoline-2-carboxylic acid formate

Conditions
ConditionsYield
Stage #1: flumequine; ethylenediamine In 1-methyl-pyrrolidin-2-one at 180℃; for 1.5h; Microwave irradiation;
Stage #2: formic acid In water; acetonitrile
42835-25-6

flumequine

75-03-6

ethyl iodide

42835-47-2

9-fluoro-5-methyl-1-oxo-6,7-dihydro-1H,5H-pyrido[3,2,1-ij]quinoline-2-carboxylic acid ethyl ester

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 70℃; for 4h;
With potassium carbonate In N,N-dimethyl-formamide at 70℃; for 4h;
3731-53-1

4-(aminomethyl)pyridine

57933-83-2

Isopropenyl chloroformate

42835-25-6

flumequine

195191-84-5

9-fluoro-6,7-dihydro-5-methyl-N-[(4-pyridyl)methyl]-1-oxo-1H,5H-benzo-[i,j]quinolizine-2-carboxamide

Conditions
ConditionsYield
With triethylamine In dichloromethane
13258-63-4

4-(2-Aminoethyl)pyridine

57933-83-2

Isopropenyl chloroformate

42835-25-6

flumequine

9-fluoro-6,7-dihydro-5-methyl-N-[2-(4-pyridyl)ethyl]-1-oxo-1H,5H-benzo-[i,j]quinolizine-2-carboxamide

Conditions
ConditionsYield
In dichloromethane
42835-25-6

flumequine

107-15-3

ethylenediamine

885696-98-0

9-[(2-aminoethyl)amino]-5-(R,S)-methyl-1-oxo-6,7-dihydro-1H,5H-pyrido[3,2,1-ij]quinoline-2-carboxylic acid

Conditions
ConditionsYield
In 1-methyl-pyrrolidin-2-one at 200℃; for 0.5h; Microwave irradiation;
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    9-Fluoro-5-methyl-1-oxo-1,5,6,7-tetrahydropyrido[3,2,1-ij]quinoline-2-carboxylic acid

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    Chemical Name 9-Fluoro-6,7-dihydro-5-methyl-1-oxo-1H,5H-benzo[ij]quinolizine-2-carboxylic acid CAS Number 42835-25-6 Molecular Formula

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Specification

1. Introduction of Flumequine

The Flumequine with cas registry number of 42835-25-6 is white crystalline solid. This chemical belongs to the following categories: Aromatics Compounds; Heterocycles; Intermediates & Fine Chemicals; Pharmaceuticals; Quinolones and Fluoroquinolones; A-K Antibiotics; Antibacterial; Chemical Structure Class; Inhibits an Enzyme Antibiotics; Interferes with DNA Synthesis Antibiotics; Mechanism of Action; Spectrum of Activity; APIs.

2. Properties of Flumequine

The physical properties about this chemical are: (1)ACD/LogP: 2.41; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 1.91; (4)ACD/LogD (pH 7.4): 0.18; (5)ACD/BCF (pH 5.5): 12.55; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 153.12; (8)ACD/KOC (pH 7.4): 2.88; (9)#H bond acceptors: 4; (10)#H bond donors: 1; (11)#Freely Rotating Bonds: 1; (12)Index of Refraction: 1.645; (13)Molar Refractivity: 65.11 cm3; (14)Molar Volume: 179.4 cm3; (15)Surface Tension: 62.3 dyne/cm; (16)Density: 1.45 g/cm3; (17)Flash Point: 219.7 °C; (18)Enthalpy of Vaporization: 73.43 kJ/mol; (19)Boiling Point: 439.7 °C at 760 mmHg; (20)Vapour Pressure: 1.66E-08 mmHg at 25°C.

3. Structure Descriptors of Flumequine

You could convert the following datas into the molecular structure:
(1)SMILES: Fc2cc1C(=O)/C(C(=O)O)=C\N3c1c(c2)CCC3C;
(2)InChI: InChI=1/C14H12FNO3/c1-7-2-3-8-4-9(15)5-10-12(8)16(7)6-11(13(10)17)14(18)19/h4-7H,2-3H2,1H3,(H,18,19);
(3)InChIKey: DPSPPJIUMHPXMA-UHFFFAOYAX

4. Safety Information of Flumequine

When you are using this chemical, please be cautious about it as the following:
As a chemical, it is irritating to eyes, respiratory system and skin. Therefore, wear suitable protective clothing, gloves and eye/face protection to avoid contact with skin and eyes when you are using it. And do not breathe dust. Take off immediately all contaminated clothing. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.

5. Use and Preparation of Flumequine

1). Preparation of Flumequine: it can be made by 9-fluoro-5-methyl-1-oxo-6,7-dihydro-1H,5H-pyrido[3,2,1-ij]quinoline-2-carboxylic acid ethyl ester with reagent water at temperature of 100 ℃.

2). Uses of Flumequine: it has been used as a drug to treat bacterial infections in farm animals, household pets, and also urinary tract infections in humans. It can kill bacteria by interfering with the enzymes that cause DNA to unwind and duplicate.