[ CAS No. 42835-25-6 ] {[proInfo.proName]}

Name: 42835-25-6|9-Fluoro-5-methyl-1-oxo-6,7-dihydro-1H,5H-pyrido[3,2,1-ij]quinoline-2-carboxylic acid|98%
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SKU: A127261
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Quality Control of [ 42835-25-6 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

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Product Details of [ 42835-25-6 ]

CAS No. :	42835-25-6	MDL No. :	MFCD00079298
Formula :	C₁₄H₁₂FNO₃	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	DPSPPJIUMHPXMA-UHFFFAOYSA-N
M.W :	261.25	Pubchem ID :	3374
Synonyms :	R-802;(±)-Flumequine	Chemical Name :	9-Fluoro-5-methyl-1-oxo-6,7-dihydro-1H,5H-pyrido[3,2,1-ij]quinoline-2-carboxylic acid

Safety of [ 42835-25-6 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 42835-25-6 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Upstream synthesis route of [ 42835-25-6 ]
Downstream synthetic route of [ 42835-25-6 ]

[ 42835-25-6 ] Synthesis Path-Upstream 1~8

1
[ 42835-89-2 ]
[ 87-13-8 ]
[ 42835-25-6 ]

Reference： [1] Patent: US4301288, 1981, A,
[2] Patent: US4301289, 1981, A,
[3] Patent: US4301291, 1981, A,

2
[ 123400-74-8 ]
[ 42835-25-6 ]

Reference： [1] Patent: EP310849, 1989, A1,

3
[ 42835-89-2 ]
[ 42835-25-6 ]

Reference： [1] Patent: US4301288, 1981, A,
[2] Patent: US4301289, 1981, A,
[3] Patent: US4301291, 1981, A,

4
[ 42835-47-2 ]
[ 42835-25-6 ]

Reference： [1] Tetrahedron Asymmetry, 1999, vol. 10, # 6, p. 1079 - 1087
[2] Journal of the American Chemical Society, 2015, vol. 137, # 36, p. 11718 - 11724

5
[ 15568-85-1 ]
[ 42835-89-2 ]
[ 123400-74-8 ]
[ 42835-25-6 ]

Reference： [1] Patent: EP310849, 1989, A1,

6
[ 42835-89-2 ]
[ 42835-25-6 ]

Reference： [1] Tetrahedron Asymmetry, 1999, vol. 10, # 6, p. 1079 - 1087
[2] Journal of the American Chemical Society, 2015, vol. 137, # 36, p. 11718 - 11724

7
[ 105450-09-7 ]
[ 42835-25-6 ]

Reference： [1] Tetrahedron Asymmetry, 1999, vol. 10, # 6, p. 1079 - 1087

8
[ 1128-61-6 ]
[ 42835-25-6 ]

Reference： [1] Journal of the American Chemical Society, 2015, vol. 137, # 36, p. 11718 - 11724

[ 42835-25-6 ] Synthesis Path-Downstream 1~46

1
[ 57933-83-2 ]
[ 42835-25-6 ]
C₁₈H₁₆FNO₅ [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,1998,vol. 8,p. 2629 - 2634

2
[ 42835-47-2 ]
[ 42835-25-6 ]

Reference： [1]Tetrahedron Asymmetry,1999,vol. 10,p. 1079 - 1087
[2]Journal of the American Chemical Society,2015,vol. 137,p. 11718 - 11724

Yield	Reaction Conditions	Operation in experiment
		Example N. 2b Flumequine preparation 9.5g (28.5 mmole) of the product of Example 2a and 18g of polyphosphoric acid are kept under stirring for 1 hour at 110-115C. The reaction mixture is cooled to about 40C, 80 ml of water are added and stirred for 1 hour at 0C. The flumequine precipitated from the mixture is filtered and washed with water to neutrality. Yield: 6.78g m.p.: 252-4C
		Example N. 5b Flumequine preparation Flumequine is prepared by heating at 110-115C under stiring for 3 hours a mixture of 5g (13.1 mmole) of the product of Example 5a, 10 g of polyphosphoric acid and 25 ml of xylene. The mixture is then treated according to the procedure of Example 1b. Yield: 2,5 g m.p.: 253-4C
		Example N. 4b Flumequine preparation Flumequine is prepared by heating under stirring at 110-115C for a few hours a mixture of 3.8g (10.3 mmole) of the product of Example 4a, 7.5 g of polyphosphoric acid and 20 ml of xylene. The mixture is then treated according to the procedure of Example 1b. Yield: 1.7g m.p.: 253-254C

Example N. 3b Flumequine preparation Flumequine is prepared according to the procedure of Example 1b, starting from 8g (23.16 mmole) of the product of Example 3a and 16g of polyphosphoric acid in 40ml of xylene. Yield: 5.6 g m.p.: 253-5C

4
[ 42835-25-6 ]
9-fluoro-5-methyl-1-oxo-6,7-dihydro-1H,5H-pyrido[3,2,1-ij]quinoline-2-carbonitrile [ No CAS ]

Reference： [1]Organic Preparations and Procedures International,2004,vol. 36,p. 597 - 600

5
[ 42835-89-2 ]
[ 42835-25-6 ]

Reference： [1]Tetrahedron Asymmetry,1999,vol. 10,p. 1079 - 1087
[2]Journal of the American Chemical Society,2015,vol. 137,p. 11718 - 11724

6
[ 105450-09-7 ]
[ 42835-25-6 ]

Reference： [1]Tetrahedron Asymmetry,1999,vol. 10,p. 1079 - 1087

7
[ 42835-25-6 ]
9-fluoro-6,7-dihydro-5-methyl-N-[2-(4-pyridyl)ethyl]-1-oxo-1H,5H-benzo-[i,j]quinolizine-2-carboxamide [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,1998,vol. 8,p. 2629 - 2634

8
[ 64-18-6 ]
[ 42835-25-6 ]
[ 887262-12-6 ]

Yield	Reaction Conditions	Operation in experiment
		Intermediate 32: 9-({2-r(2-Hvdroxyethyl)oxylethyl}amino)-5-methyl-1 -oxo-6,7- dihvdro-1f/.5H-pyridor3,2,1-//1quinoline-2-carboxylic acid formate salt A suspension of <strong>[42835-25-6]flumequine</strong> (0.261 g) and 2-[(2-aminoethyl)oxy]ethanol (1.2 mL) in N- methylpyrrolidinone (1.2 mL) was microwaved at 220C for 1 h. The reaction mixture was purified by mass directed automatic preparative HPLC to give the title compound as a yellow solid (0.152 g); ESMS m/z 347.3 [M+H]+. EPO <DP n="65"/>t>4

Reference： [1]Patent: WO2006/50940,2006,A1 .Location in patent: Page/Page column 63

9
[ 64-18-6 ]
[ 42835-25-6 ]
[ 887262-13-7 ]

Yield	Reaction Conditions	Operation in experiment
		Intermediate 33: 9-({2-f(2-Aminoethyl)oxy1ethyl>amino)-5-methyl-1 -oxo-6J-dihydro- 1H,5H-pyridor3,2,1-//lquinoline-2-carboxylic acid formate saltA suspension of <strong>[42835-25-6]flumequine</strong> (0.13 g) and {2-[(2-aminoethyl)oxy]ethyl}amine (0.25 mL) in N-methylpyrrolidinone (0.25 mL) was microwaved at 2000C for 1 h. The reaction mixture was purified by mass directed automatic preparative HPLC to give the title compound as a yellow oil (0.144 g) containing some N-methylpyrrolidinone; ESMS m/z 346.4 [M+H]+.

Reference： [1]Patent: WO2006/50940,2006,A1 .Location in patent: Page/Page column 64

10
[ 64-18-6 ]
[ 42835-25-6 ]
[ 887262-24-0 ]

Yield	Reaction Conditions	Operation in experiment
		Intermediate 42: 9-r(2-Aminoethyl)aminol-5-methyl-1-oxo-6,7-dihvdro-1H,5H- pyridor3,2,1-//lquinoline-2-carboxylic acid formate salt A suspension of <strong>[42835-25-6]flumequine</strong> (0.522 g) and 1 ,2-diaminoethane (0.668 mL) in N- methylpyrrolidinone (1 mL) was microwaved at 180C for 1.5 h. The reaction mixture was purified by mass directed automatic preparative HPLC to give the title compound as a yellow solid (0.35 g); ESMS m/z 302.3 [M+H]+.

Reference： [1]Patent: WO2006/50940,2006,A1 .Location in patent: Page/Page column 72

11
[ 42835-25-6 ]
[ 75-03-6 ]
[ 42835-47-2 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; In N,N-dimethyl-formamide; at 70℃; for 4h;	a) 9-Fluoro-5-methyl-1 -oxo-6,7-dihydro-1 H,5H-pyrido[3,2,1 -//]quinoline-2-carboxylic acid ethyl ester; A suspension of <strong>[42835-25-6]flumequine</strong> (1.045 g), ethyl iodide(3.1 mL) and potassium carbonate (2.75 g) in DMF (50 mL) was heated at 700C for 4 h. The reaction mixture was concentrated in vacuo. The residue was preabsorbed on silica gel and purified by chromatography (silica gel, 0 to 1% [9:1 MeOH/20M aqueous ammonia] in DCM to give the title compound as a white solid (1.1 g); ESMS m/z 290.3 [M+Hf.
	With potassium carbonate; In N,N-dimethyl-formamide; at 70℃; for 4h;	Intermediate 1 :; 9-r(2-Aminoethyl)thio1-5-(R,S)-methyl-1 -oxo-6.7-dihvdro-1 H,5H- pyridof3,2,1-//lquinoline-2-carboxylic acid trifluoroacetate salt; a) Ethyl 9-fluoro-5-(R,S)-methyl-1-oxo-6,7-dihydro-1H,5H-pyrido[3,2,1- /y]quinoline-2-carboxylate; A suspension of <strong>[42835-25-6]flumequine</strong> (1.045 g, 4 mmol), iodoethane (3.1 mL, 40 mmol) and potassium carbonate (2.75 g, 20 mmol) in dimethylformamide (50 mL) was heated at 700C for 4 h. The reaction mixture was concentrated in vacuo. The residue was pre-absorbed on silica gel and purified by chromatography (silica gel, 0 to 5% [9:1 methanol/20 M ammonia] in dichloromethane) to give the title compound as a white solid (1.1 g); ESMS m/z 290.3 [M+H]+.

Reference： [1]Patent: WO2006/50940,2006,A1 .Location in patent: Page/Page column 50
[2]Patent: WO2006/50941,2006,A1 .Location in patent: Page/Page column 35

12
[ 3731-53-1 ]
[ 57933-83-2 ]
[ 42835-25-6 ]
[ 195191-84-5 ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; In dichloromethane;	EXAMPLE 3 9-fluoro-6,7-dihydro-5-methyl-N-[(4-pyridyl)methyl]-1-oxo-1H,5H-benzo-[i,j]quinolizine-2-carboxamide <strong>[42835-25-6]Flumequine</strong> (0.46 g) and dichloromethane (16.3 ml) were combined under nitrogen and cooled to 0 C. Triethylamine (0.27 ml) was then added dropwise, followed by isopropenylchloroformate (0.21 ml) and the whole stirred for 60 minutes. 4-(Aminomethyl)pyridine (0.2 ml) was then added and the reaction stirred for 20 h, after which time it was diluted with dichloromethane, washed with water (3 times), dried (MgSO4), concentrated in vacuo and triturated with acetone to give the title compound (0.49 g) as a yellow solid. TLC Rf =0.43 (10% MeOH/CH2 Cl2) m.p.=199-200 C.

Reference： [1]Patent: US5792774,1998,A

13
[ 13258-63-4 ]
[ 57933-83-2 ]
[ 42835-25-6 ]
9-fluoro-6,7-dihydro-5-methyl-N-[2-(4-pyridyl)ethyl]-1-oxo-1H,5H-benzo-[i,j]quinolizine-2-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In dichloromethane;	EXAMPLE 1 9-fluoro-6,7-dihydro-5-methyl-N-[2-(4-pyridyl)ethyl]-1-oxo-1H,5H-benzo-[i,j]quinolizine-2-carboxamide <strong>[42835-25-6]Flumequine</strong> (0.46 g) and dichloromethane (16.3 ml) were combined under nitrogen and cooled to 0 C. Triethylamnine (0.27 ml) was then added dropwise, followed by isopropenyl chloroformate (0.21 ml) and the whole stirred for 60 minutes. 4-(2-Aminoethyl)pyridine (0.23 ml) was then added and the reaction stirred for 20 h, concentrated onto silica and purified by flash column chromatography to give the title compound (0.55 g) as a white solid. TLC Rf =0.27 (5% MeOH/CH2 Cl2) mp=217 C.

Reference： [1]Patent: US5792774,1998,A

14
[ 42835-25-6 ]
[ 107-15-3 ]
[ 885696-98-0 ]

Yield	Reaction Conditions	Operation in experiment
	In 1-methyl-pyrrolidin-2-one; at 200℃; for 0.5h;Microwave irradiation;	Intermediate 12:; 9-r(2-aminoethyl)amino1-5-(RS)-methyl-1-oxo-6,7-dihvdro-1H,5H- pyridor3,2,1 -//lquinoline-2-carboxylic acid; A solution of <strong>[42835-25-6]flumequine</strong> (0.26 g, 1 mmol) and 1 ,2-diaminoethane (0.334 mL) in Lambda/-methyl- 2-pyrrolidinone (0.5 mL) was microwaved at 2000C for 0.5 h. The reaction mixture was concentrated then purified by preparative reverse phase HPLC (MeCN/H2O/0.1%HCO2H eluent) to give the title compound as a pale yellow solid (0.15 g). ESMS m/z 302.3 [M+H]+.

Reference： [1]Patent: WO2006/50941,2006,A1 .Location in patent: Page/Page column 40

15
[ 2752-17-2 ]
[ 42835-25-6 ]
[ 869311-04-6 ]

Yield	Reaction Conditions	Operation in experiment
	In 1-methyl-pyrrolidin-2-one; at 200℃; for 1h;Microwave irradiation;	Intermediate 11; : 9-({2-r(2-aminoethyl)oxylethyl)amino)-5-(ft,S)-methyl-1 -oxo-6 J- dihvdro-1H,5H-pyridor3,2,1-//]quinoline-2-carboxylic acid; A solution of <strong>[42835-25-6]flumequine</strong> (0.13 g, 0.5 mmol) and {2-[(2-aminoethyl)oxy]ethyl}amine (0.25 mL) in Lambda/-methyl-2-pyrrolidinone (0.25 mL) was microwaved at 2000C for 1 h. The reaction mixture was purified by preparative reverse phase HPLC (MeCN/H2O/0.1%HCO2H eluent) to give the title compound as a yellow oil (0.14 g). ESMS m/z 346.4 [M+H]+.

Reference： [1]Patent: WO2006/50941,2006,A1 .Location in patent: Page/Page column 40

16
[ 42835-89-2 ]
[ 87-13-8 ]
[ 42835-25-6 ]

Yield	Reaction Conditions	Operation in experiment
	With PPA; In water; toluene;	EXAMPLE 3 A mixture of 606 kg of diethyl ethoxymethylenemalonate and 400 kg of 6-fluorotetrahydroquinaldine was stirred and heated at about 125 C. for 5 hours. The mixture was cooled to about 95 C. and evaporated. To the stirred reaction mixture was added 450 liters of toluene, then 908 kg of polyphosphoric acid at a rate to maintain a reaction temperature of 90 to 100 C. The mixture was then heated at reflux for fourteen hours. To this mixture was added 950 liters of water over five hours. The ester was saponified by heating for 13 hours at 110 to 115 C. while removing the toluene via the toluene-water azeotrope. The solid product flumequine was separated by filtration, washed thrice with hot water, then with N,N-dimethylformamide. Recrystallization form N,N-dimethylformamide gave white solid flumequine.
	In sodium hydroxide; toluene;	EXAMPLE 2 6-Fluorotetrahydroquinaldine (12.05 kg containing 10% of toluene) and diethyl ethoxymethylene malonate (16.2 kg) were charged to a 225 liter Pfaudler reactor and heated at 125 C. under vacuum for 4 hours. Ethanol (3.1 kg) was recovered. The product was cooled, diluted with toluene (35 liters) and tetraphosphoric acid (35 kg), reheated to reflux for 2 hours, cooled to 80 C., diluted with water (128 liters) and refluxed for 6 hours to complete the hydrolysis. The crude flumequine was collected, washed acid free with water and rinsed with methanol. The damp cake was dissolved in sodium hydroxide solution (2.94 kg/59 liters) filtered hot through a cartridge filter heated to 90 C. and acidified with hydrochloric acid (6.64 liters). The product was collected, washed acid free, rinsed with methanol and dried in a vacuum oven. The yield of flumequine was 15.4 kg (90.8%). The dry solid was dissolved in N,N-dimethylformamide (70 liters) at 125 C., allowed to cool with stirring to 100 C. then cooled to 7 C. with cold water. The product was collected, washed with methanol and dried as before. The yield of recrystallized flumequine was 14.4 kg (82.3%) overall.
	With PPA; In water; toluene;	EXAMPLE 4 A mixture of 606 kg of diethyl ethoxymethylenemalonate and 400 kg of 6-fluorotetrahydroquinaldine was stirred and heated at about 125 C. for 5 hours. The mixture was cooled to about 95 C. and evaporated. To the stirred reaction mixture was added 450 liters of toluene, then 908 kg of polyphosphoric acid at a rate to maintain a reaction temperature of 90 to 100 C. The mixture was then heated at reflux for fourteen hours. To this mixture was added 950 liters of water over five hours. The ester was saponified by heating for 13 hours at 110 to 115 C. while removing the toluene via the toluene-water ezeotrope. The solid product flumequine was separated by filtration, washed thrice with hot water, then with N,N-dimethylformamide. Recrystallization form N,N-dimethylformamide gave white solid flumequine.

In sodium hydroxide; toluene;

EXAMPLE 3 6-Fluorotetrahydroquinaldine (12.05 kg containing 10% of toluene) and diethyl ethoxymethylene malonate (16.2 kg) were charged to a 225 liter Pfaudler reactor and heated at 125 C. under vacuum for 4 hours. Ethanol (3.1 kg) was recovered. The product was cooled, diluted with toluene (35 liters) and tetraphosphoric acid (35 kg), reheated to reflux for 2 hours, cooled to 80 C., diluted with water (128 liters) and refluxed for 6 hours to complete the hydrolysis. The crude flumequine was collected, washed acid free with water and rinsed with methanol. The damp cake was dissolved in sodium hydroxide solution (2.94 kg/59 liters) filtered hot through a cartridge filter heated to 90 C. and acidified with hydrochloric acid (6.64 liters). The product was collected, washed acid free, rinsed with methanol and dried in a vacuum oven. The yield of flumequine was 15.4 kg (90.8%). The dry solid was dissolved in N,N-dimethylformamide (70 liters) at 125 C., allowed to cool with stirring to 100 C. then cooled to 7 C. with cold water. The product was collected, washed with methanol and dried as before. The yield of recrystallized flumequine was 14.4 kg (82.3%) overall.

Reference： [1]Patent: US4301288,1981,A
[2]Patent: US4301288,1981,A
[3]Patent: US4301289,1981,A
[4]Patent: US4301289,1981,A

17
[ 42835-25-6 ]
sodium 6,7-dihydro-9-fluoro-5-methyl-1-oxo-1H,5H-benzo[ij]-quinolizine-2-carboxylate hydrate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydroxide; In methanol; diethyl ether; ethanol; water;	EXAMPLE 55 6,7-Dihydro-9-fluoro-5-methyl-1-oxo-1H,5H-benzo[ij]-quinolizine-2-carboxylic acid (31 g., 0.12 mole), sodium hydroxide (4.75 g., 0.12 mole) and ethanol (300 ml.) are mixed, and about 85 ml. of water are added with stirring. After 1 hour the mixture is filtered, then the filtrate is evaporated to dryness. The residue is azeotroped twice with an ethanol-benzene mixture. The solid is dissolved in methanol, the solution is filtered, and the product is precipitated by the addition of diethyl ether. The product is sodium 6,7-dihydro-9-fluoro-5-methyl-1-oxo-1H,5H-benzo[ij]quinolizine-2-carboxylate hydrate, m.p. >195 C. Analysis: Calculated for C14 H11 FNNaO3.3/4 H2 O: C,56.8; H,4.3; N,4.7. Found: C,56.6; H,4.4; N,4.7.

Reference： [1]Patent: US3969463,1976,A

18
[ 42835-25-6 ]
[ 42835-69-8 ]

Yield	Reaction Conditions	Operation in experiment
	With thionyl chloride;	A. Preparation of an acyl chloride derivative. 6,7-Dihydro-9-fluoro-5-methyl-1-oxo-1H,5H-benzo[ij]-quinolizine-2-carboxylic acid (5.0 g., 0.0192 mole) is stirred with thionyl chloride (75 ml.), and the mixture is heated to its reflux temperature and maintained at reflux for about 18 hours. The mixture is evaporated to dryness, then azeotroped thrice with 50 ml. portions of benzene to provide an off-white solid, 6,7-dihydro-9-fluoro-5-methyl-1-oxo-1H,5H-benzo[ij]quinolizine-2-carboxyl chloride, m.p. 183-186 C.

Reference： [1]Patent: US3969463,1976,A

19
[ 15568-85-1 ]
[ 42835-89-2 ]
[ 123400-74-8 ]
[ 42835-25-6 ]

Yield	Reaction Conditions	Operation in experiment
	In tetrahydrofuran;	Example N. 6 Preparation of 5- [1-(6-fluoro-2-methyl-1,2,3,4-tetrahydroquinolyl) ] -methylene-2,2-dimethyl 1,3-dioxan-4,6-dione 1.65 g (10 mmole) of 6-fluoro-2-methyl-1,2-3,4-tetrahydroquinoline and 2,05 g (11 mmole) of 2,2-dimethyl-5-methoxymethylene-1,3-dioxan-4,6-dione [prepared according to Monatshafte fuer Chemie, 98 , 565 (1967)] are reached under stirring and heating at 100-110C for 1 hour. The cooled reaction mass is taken up in tetrahydrofurane and the solids are filtered and dried. Yield: 2.5 g m.p.: 163-5C Flumequine is prepared from the resulting product according to the procedure of Example 1b.

Reference： [1]Patent: EP310849,1989,A1

20
[ 123400-74-8 ]
[ 42835-25-6 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydroxide; PPA; In 5,5-dimethyl-1,3-cyclohexadiene;	Example N. 1b Flumequine preparation 3.99 g (12.5 mmole) of 5-[1-(6-fluoro-2-methyl -1,2,3,4-tetrahydroquinolyl)] -methylene-2,2-dimethyl-1,3-dioxan-4,6-dione, 8g of polyphosphoric acid and 20 ml of xylene are heated to 110-115C under vigorous stirring. After 1 hour of heating under stirring, the reaction mixture is cooled to about room temperature and 10% aqueous sodium hydroxide is added up to pH 8.5-9. The mixture is allowed to return to room temperature under stirring, the organic layer is separated and the aqueous alkaline solution is washed a few times with ethyl ether. The alkaline solution is cooled in an ice-bath and acidified to pH 3 with concentrated HCl. The resulting precipitate is filtered and washed with water. Yield: 3.05 g m.p.: 253-5C The product is identical (m.p., IR, TLC) with a true flumequine sample and is pure enough so that further treatments are not necessary.

Reference： [1]Patent: EP310849,1989,A1

21
[ 95-14-7 ]
[ 42835-25-6 ]
[ 1173208-75-7 ]

Reference： [1]Organic and Biomolecular Chemistry,2009,vol. 7,p. 2359 - 2362

23
zinc nitrate tetrahydrate [ No CAS ]
[ 42835-25-6 ]
[ 1268154-95-5 ]

Reference： [1]Polyhedron,2011,vol. 30,p. 438 - 443

24
copper(II) nitrate trihydrate [ No CAS ]
[ 42835-25-6 ]
[ 1268154-93-3 ]

Reference： [1]Polyhedron,2011,vol. 30,p. 438 - 443

25
[ 366-18-7 ]
[ 42835-25-6 ]
potassium hydroxide [ No CAS ]
[ 7646-85-7 ]
[(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 [ No CAS ]

Reference： [1]New Journal of Chemistry,2013,vol. 37,p. 342 - 355

26
[ 42835-25-6 ]
[ 7646-85-7 ]
[ 1268236-43-6 ]

Reference： [1]New Journal of Chemistry,2013,vol. 37,p. 342 - 355

27
[ 366-18-7 ]
[ 42835-25-6 ]
[ 7646-85-7 ]
[(2,2'-bipyridine)chlorido(flumequinato-k²O,O')zinc(II)] [ No CAS ]

Reference： [1]New Journal of Chemistry,2013,vol. 37,p. 342 - 355

28
[ 67-56-1 ]
[ 66-71-7 ]
[ 42835-25-6 ]
[ 7646-85-7 ]
[Zn(flmq)(phen)Cl]*0.5MeOH [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
65%		General procedure: Oxolinic acid (0.4 mmol, 105 mg) dissolved in CH3OH (10 mL) was deprotonated by KOH (0.4 mmol, 22 mg). The resultant solution was stirred for about 20 min at ambient temperature. The solution of deprotonated oxolinic acid and a methanolic solution (5 mL) of phen (0.4 mmol, 72 mg) were added simultaneously dropwise to a methanolic solution (5 mL) of ZnCl2 (0.4 mmol, 56 mg). The reaction mixture was stirred for about 1 h and left for slow evaporation. Colorless crystals of [Zn(oxo)(phen)Cl] · MeOH, 1 · MeOH, suitable for X-ray structure determination were collected after a few days. Yield: 170 mg, 75%. Anal. Calcd. for [Zn(oxo)(phen)Cl] · MeOH (C26H22N3O6ClZn) (MW = 573.31): C 54.47, H 3.87, N 7.33; found C 54.31, H 4.05, N 6.95. IR (KBr pellet): numax/cm- 1 nu(C = O)pyridone 1641(very strong (vs)); nuasym(CO2): 1597(vs); nusym(CO2): 1392(vs); Delta = nuasym(CO2) - nusym(CO2): 205 cm- 1; UV-vis: lambda/nm (epsilon/M- 1 cm- 1) as nujol mull: 340, 325, 293; in DMSO: 338 (8200), 324 (8500), 293 (10400). 1H-NMR: delta (300 MHz; d6-DMSO): 1.38 (3H, t, H1b-oxo), 4.52 (2H, m, H1a-oxo), 6.28 (2H, s, H12-oxo), 7.58 (2H, s, H5- and H8-oxo), 7.65 (2H, d, H3- and H8-phen), 8.08 (2H, s, H5- and H6-phen), 8.25 (2H, s, H4- and H7-phen), 8.89 (2H, d, H2- and H9-phen), 8.99 (1H, s, H2-oxo). The complex is soluble in N,N-dimethylformamide (DMF) and DMSO (LambdaM = 14 mho cm2 mol- 1, in 1 mM DMSO solution).

Reference： [1]Journal of Inorganic Biochemistry,2013,vol. 121,p. 53 - 65

29
[ 67-56-1 ]
[ 66-71-7 ]
[ 42835-25-6 ]
[ 7646-85-7 ]
[Zn(flmq)2(phen)]*2MeOH [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
60%	With potassium hydroxide;	A methanolic solution (10 mL) containing <strong>[42835-25-6]flumequine</strong> (0.4 mmol, 105 mg) and KOH (0.4 mmol, 22 mg) and a methanolic solution (5 mL) of phen (0.2 mmol, 36 mg) were added simultaneously and dropwise to a methanolic solution (5 mL) of ZnCl2 (0.2 mmol, 28 mg). The reaction mixture was stirred for 1 h and left for slow evaporation. Colorless crystals of [Zn(flmq)2(phen)] · MeOH, 5 · 2MeOH, suitable for X-ray structure determination were deposited after a few days. Yield: 95 mg, 60%. Anal. Calcd. for [Zn(flmq)2(phen)] · 2MeOH (C42H38F2N4O8Zn) (MW = 830.13): C 60.77, H 4.61, N 6.74; found C 61.31, H 4.39, N 6.85. IR (KBr pellet): numax/cm- 1 nu(C = O)pyridone 1637(vs); nuasym(CO2): 1590(vs); nusym(CO2): 1373(vs); Delta = 217 cm- 1; UV-vis: lambda/nm (epsilon/M- 1 cm- 1) as nujol mull: 340, 325, 295; in DMSO: 340 (15100), 326 (18500), 296 (16100). 1H-NMR: delta (300 MHz; (5:1) d6-DMSO:CDCl3): 1.38 (6H, d, H10a-flmq), 2.10 (4H, d, H8-flmq), 3.10 (4H, m, H9-flmq), 4.68 (2H, m, H10-flmq), 7.35 (2H, d, H7-flmq), 7.53 (2H, m, H5-flmq), 7.92 (2H, q, H3- and H8-phen), 8.10 (2H, s, H5- and H6-phen), 8.67 (2H, d, H4- and H7-phen), 8.92 (2H, d, H2- and H9-phen), 9.17 (2H, s, H2-flmq). Complex 5 is soluble in DMSO (LambdaM = 11 mho cm2 mol- 1, in 1 mM DMSO solution).

Reference： [1]Journal of Inorganic Biochemistry,2013,vol. 121,p. 53 - 65

30
zinc acetate hydrate [ No CAS ]
[ 100-21-0 ]
[ 7732-18-5 ]
[ 42835-25-6 ]
[Zn₂(flmq)₂(bdc)(H₂O)₂] [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
48%	With potassium hydroxide; at 150℃; for 72h;Autoclave; High pressure;	A mixture of Zn(OAc)2?H2O (87mg, 0.4mmol), Hflmq (52mg, 0.2mmol), H2bdc (33mg, 0.2mmol) and distilled water (8ml) was adjusted to pH with KOH (22mg, 0.4mmol) solution and then sealed in an 18ml Teflon-lined autoclave which was heated in an oven at 150C for 72h. After slow cooling to room temperature, brown block crystals of 1 were separated by filtration, washed with distilled water and dried at ambient temperature (Yield 48% based on Zn). Elemental analysis: Calcd. for C36H30F2N2O12Zn2: C, 50 .74; H, 3.52; N, 3.29. Found: C, 51.20; H, 4.05; N,3.52%. IR (KBr,cm-1): 1385s, 1390vs, 1587vs, 1589s, 1625s, 1630vs.

Reference： [1]Inorganic Chemistry Communications,2014,vol. 46,p. 180 - 183

31
[ 1128-61-6 ]
[ 42835-25-6 ]

Reference： [1]Journal of the American Chemical Society,2015,vol. 137,p. 11718 - 11724

32
[ 66-71-7 ]
cobalt(II) chloride hexahydrate [ No CAS ]
[ 42835-25-6 ]
C₄₀H₃₀CoF₂N₄O₆*1.6CH₄O*0.4H₂O [ No CAS ]

Reference： [1]RSC Advances,2016,vol. 6,p. 19555 - 19570

33
[ 366-18-7 ]
cobalt(II) chloride hexahydrate [ No CAS ]
[ 42835-25-6 ]
C₃₈H₃₀CoF₂N₄O₆*H₂O [ No CAS ]

Reference： [1]RSC Advances,2016,vol. 6,p. 19555 - 19570

34
[ 1202-34-2 ]
cobalt(II) chloride hexahydrate [ No CAS ]
[ 42835-25-6 ]
C₃₈H₃₁CoF₂N₅O₆*H₂O [ No CAS ]

Reference： [1]RSC Advances,2016,vol. 6,p. 19555 - 19570

35
[ 67-56-1 ]
cobalt(II) chloride hexahydrate [ No CAS ]
[ 42835-25-6 ]
Co⁽²⁺⁾*2CH₄O*2C₁₄H₁₁FNO₃^(1-) [ No CAS ]

Reference： [1]RSC Advances,2016,vol. 6,p. 19555 - 19570

36
[ 42835-25-6 ]
[ 215178-95-3 ]
S-(-)-flumequine [ No CAS ]

Reference： [1]Chirality,2016,p. 649 - 655
[2]Chirality,2018,vol. 30,p. 1304 - 1311

37
[ 67-56-1 ]
manganese(II) chloride tetrahydrate [ No CAS ]
[ 42835-25-6 ]
C₃₀H₃₀F₂MnN₂O₈ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
60%		A methanolic solution (10mL) of <strong>[42835-25-6]flumequine</strong> (0.4mmol, 104mg) and KOH (0.4mmol, 22mg) was stirred for 30min. Afterwards, the solution was added slowly to a methanolic solution (10mL) of MnCl2·4H2O (0.2mmol, 40mg) followed by a 30-min stirring. The resultant solution was left for slow evaporation. Yellowish microcrystalline product of [Mn(flmq)2(MeOH)2] 1 (75mg, yield: 60%) was collected after two weeks. ESI-MS(+), m/z: found, 672.45 (Fig. S1(A)); calc. for [1+H]+·MeOH, 674.60. Anal. Calc. for [Mn(flmq)2(MeOH)2] (C30H30MnF2N2O8, MW=639.51) C, 56.34; H, 4.73; N, 4.38; found: C, 56.26; H, 4.68; N, 4.46%. IR (KBr disk): numax, cm-1; nu(C=O)pyridone, 1624 (vs(very strong)); vasym(CO2), 1577 (vs); nusym(CO2), 1374 (s(strong)); Deltanu(CO2)=nuasym(CO2)-nusym(CO2): 203cm-1. UV-Vis: as Nujol mull, lambda/nm: 342 (sh (shoulder), 329 (sh), 305; in DMSO, lambda/nm (epsilon/M-1cm-1): 343 (6200), 330 (6500), 304 (4600). mueff at room temperature=5.94 BM. The complex is soluble in DMF and DMSO (LambdaM=8 S·cm2·mol-1, in 1mM DMSO solution) and partially soluble in methanol and acetonitrile.

Reference： [1]Polyhedron,2018,vol. 145,p. 166 - 175

38
[ 67-56-1 ]
[ 66-71-7 ]
manganese(II) chloride tetrahydrate [ No CAS ]
[ 42835-25-6 ]
[Mn(flmq)₂(1,10-phenanthroline)]*2MeOH [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
65%		The methanolic solution (15mL) containing <strong>[42835-25-6]flumequine</strong> (0.4mmol, 104mg) and KOH (0.4mmol, 22mg) was added, after a 30-min stirring, slowly and simultaneously with a methanolic solution of phen (0.2mmol, 36mg) to a methanolic solution (10mL) of MnCl2·4H2O (0.2mmol, 40mg). The resultant solution was stirred for 15min and left for slow evaporation. Yellow crystals of [Mn(flmq)2(phen)], 2 (98mg, yield: 65%) suitable for X-ray structure determination, were collected after a few days. ESI-MS(+), m/z: found, 853.81 (Fig. S1(B)); Calc. for [2+H]+·3MeOH, 856.51. Anal. Calc. for [Mn(flmq)2(phen)] (C40H30MnF2N4O6, MW=755.64): C, 63.58; H, 4.00; N, 7.42; found: C, 63.42; H, 4.11; N, 7.51%; IR (KBr disk): numax/cm-1 nu(C=O)pyridone 1625 (vs); nuasym(CO2): 1588 (vs); nusym(CO2): 1373(s); Deltanu(CO2)=215cm-1; rho(C-H)bipyam: 732. UV-Vis: as Nujol mull, lambda/nm: 342, 328, 305(sh); in DMSO, lambda/nm (epsilon/M-1cm-1): 342 (11400), 330 (10600), 306 (7500). mueff at room temperature=5.97BM. The complex is soluble in DMSO (LambdaM=9S·cm2·mol-1, in 1mM DMSO solution) and partially soluble in DMF and MeOH.

Reference： [1]Polyhedron,2018,vol. 145,p. 166 - 175

39
[ 1202-34-2 ]
manganese(II) chloride tetrahydrate [ No CAS ]
[ 42835-25-6 ]
Mn(flmq)₂(2,2′-bipyridylamine) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
60%		General procedure: The methanolic solution (15mL) containing <strong>[42835-25-6]flumequine</strong> (0.4mmol, 104mg) and KOH (0.4mmol, 22mg) was added, after a 30-min stirring, slowly and simultaneously with a methanolic solution of phen (0.2mmol, 36mg) to a methanolic solution (10mL) of MnCl2·4H2O (0.2mmol, 40mg). The resultant solution was stirred for 15min and left for slow evaporation. Yellow crystals of [Mn(flmq)2(phen)], 2 (98mg, yield: 65%) suitable for X-ray structure determination, were collected after a few days.

Reference： [1]Polyhedron,2018,vol. 145,p. 166 - 175

40
[ 1067-97-6 ]
[ 42835-25-6 ]
C₂₆H₃₈FNO₃Sn [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In toluene;Dean-Stark; Reflux;	General procedure: Stoichiometric quantities of the respective medicinal ligands (HL1 and HL2) and theappropriate organotin hydroxide (trimethyltin, tributyltin and triphenyltin) in toluene were refluxedin a two-necked flask fitted with a Dean and Stark apparatus for 12-15 h with continuousazeotropic removal of water. The progress of the reaction was monitored through thinlayer chromatography. The reaction mixture was allowed to cool to room temperature andthen evaporated under reduced pressure until the formation of a thick concentrate, which wasallowed to solidify normally. The crude synthesized products were recrystallized using a mixtureof n-hexane:chloroform (1:4) to obtain the target products 1-6 in powder form.

Reference： [1]Journal of the Serbian Chemical Society,2018,vol. 83,p. 425 - 437

41
[ 76-87-9 ]
[ 42835-25-6 ]
C₃₂H₂₆FNO₃Sn [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In toluene;Dean-Stark; Reflux;	General procedure: Stoichiometric quantities of the respective medicinal ligands (HL1 and HL2) and theappropriate organotin hydroxide (trimethyltin, tributyltin and triphenyltin) in toluene were refluxedin a two-necked flask fitted with a Dean and Stark apparatus for 12-15 h with continuousazeotropic removal of water. The progress of the reaction was monitored through thinlayer chromatography. The reaction mixture was allowed to cool to room temperature andthen evaporated under reduced pressure until the formation of a thick concentrate, which wasallowed to solidify normally. The crude synthesized products were recrystallized using a mixtureof n-hexane:chloroform (1:4) to obtain the target products 1-6 in powder form.

Reference： [1]Journal of the Serbian Chemical Society,2018,vol. 83,p. 425 - 437

42
[ 42835-25-6 ]
[ 56-24-6 ]
C₁₇H₂₀FNO₃Sn [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In toluene;Dean-Stark; Reflux;	General procedure: Stoichiometric quantities of the respective medicinal ligands (HL1 and HL2) and theappropriate organotin hydroxide (trimethyltin, tributyltin and triphenyltin) in toluene were refluxedin a two-necked flask fitted with a Dean and Stark apparatus for 12-15 h with continuousazeotropic removal of water. The progress of the reaction was monitored through thinlayer chromatography. The reaction mixture was allowed to cool to room temperature andthen evaporated under reduced pressure until the formation of a thick concentrate, which wasallowed to solidify normally. The crude synthesized products were recrystallized using a mixtureof n-hexane:chloroform (1:4) to obtain the target products 1-6 in powder form.

Reference： [1]Journal of the Serbian Chemical Society,2018,vol. 83,p. 425 - 437

43
[ 42835-25-6 ]
¹³C-9-fluoro-5-methyl-1-oxo-6,7-dihydro-1H,5H-pyrido[3,2,1-ij]quinoline-2-carboxylic acid [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2019,vol. 141,p. 780 - 784

44
[ 42835-25-6 ]
¹⁴C-9-fluoro-5-methyl-1-oxo-6,7-dihydro-1H,5H-pyrido[3,2,1-ij]quinoline-2-carboxylic acid [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2019,vol. 141,p. 780 - 784

45
[ 42835-25-6 ]
9-fluoro-5-methyl-1-oxo-6,7-dihydro-1H,5H-pyrido[3,2,1-ij]quinoline-2-carboxylic acid cesium salt [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2019,vol. 141,p. 780 - 784

46
[ 42835-25-6 ]
Chiralpak IC, 250 mm × 4.6mm, i.d. 5 μm [ No CAS ]
[ 215178-95-3 ]
S-(-)-flumequine [ No CAS ]

Reference： [1]Chirality,2019,vol. 31,p. 968 - 978

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H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
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H222	Extremely flammable aerosol
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H250	Catches fire spontaneously if exposed to air
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Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
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Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
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H410	Very toxic to aquatic life with long-lasting effects
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H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

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Quality Control of [ 42835-25-6 ]

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Product Details of [ 42835-25-6 ]

Safety of [ 42835-25-6 ]

Application In Synthesis of [ 42835-25-6 ]

[ 42835-25-6 ] Synthesis Path-Upstream 1~8

[ 42835-25-6 ] Synthesis Path-Downstream 1~46

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