7-Chloro-1-ethyl-6-fluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid
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7-Chloro-1-ethyl-6-fluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid
structure -
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CAS No:
68077-26-9
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Formula:
C12H9ClFNO3
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Chemical Name:
7-Chloro-1-ethyl-6-fluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid
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Synonyms:
3-Quinolinecarboxylic acid,7-chloro-1-ethyl-6-fluoro-1,4-dihydro-4-oxo-;7-Chloro-1-ethyl-6-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid;CGA 78039;7-Chloro-1-ethyl-6-fluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid;7-Chloro-1,4-dihydro-1-ethyl-6-fluoro-4-oxo-3-quinolinecarboxylic acid;M 193324;1-Ethyl-7-chloro-6-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid;1-Ethyl-1,4-dihydro-4-oxo-6-fluoro-7-chloro-3-quinolinecarboxylic acid;7-Chloro-1-ethyl-6-fluoroquinolin-4-one-3-carboxylic acid;7-Chloro-1-ethyl-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid;1-Ethyl-6-fluoro-7-chloro-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid;1-Ethyl-6-fluoro-7-chloro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid
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CAS No:
7-Chloro-1-ethyl-6-fluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid Basic Attributes
269.66
269.66
421-280-4
831B5OC9PQ
DTXSID90333112
2933499090
Characteristics
57.6
2.4
1.5±0.1 g/cm3
208-210 °C
437.9°C at 760 mmHg
218.7±28.7 °C
1.601
Refrigerator
Safety Information
IRRITANT
52/53
61
P261, P264, P271, P273, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, P501
H315
|Warning|H315 (33.33%): Causes skin irritation [Warning Skin corrosion/irritation]|P261, P264, P271, P273, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, and P501|Aggregated GHS information provided by 15 companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
7-Chloro-1-ethyl-6-fluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid Use and Manufacturing
Ethyl quinolinate(2.75 g, 9.24 mmol) was dissolved in 60 mL of methanol, Added 1:1 hydrochloric acid (31.5 mL, 189 mmol).After refluxing for 2 hours, a white solid precipitated and was filtered.Wash with plenty of water, vacuum oven drying for 2 hours, The product quinolinic acid (2.46 g, yield: 89.5percent) was obtained.In a 100 mL, 3 -neck round-bottomed flask, the intermediate (3) (1.0 g, 3.36 mmol) from Example 6 was charged with THF: Water (4: 1) (20 mL). To this reaction mixture, a 2M NaOH solution (6 mL) was added dropwise maintaining the temperature at room temperature. The reaction mixture was stirred at 80 °C for 2h and then cooled to 0 °C followed by acidification to pH 3-4 by 4N HCl. The solid obtained was filtered to obtain the crude product. The crude product was extracted with ethyl acetate (50 mL x 3). The combined organic layer was washed with brine solution, dried over anhydrous NaA mixture of 7-chloro-6-fluoro-4-hydroxyquinoline-3-carboxylic acid ethyl ester (4) (55.0 g), anhydrous potassium carbonate (8.0 g) and DMF (150 mL) was heated with stirring at 125° C. for 3 h. It was cooled to 70° C. and ethyl iodide (19.0 g) was added and continued heating at 120° C. for 4 h. The mixture was evaporated to dryness, extracted, with CHA process according to claim 1, wherein the quinolonecarboxylic acid ester is a methyl or ethyl ester of a carboxylic acid selected from the group consisting of ... 1-cyclopropyl-6-fluoro-1, 4-dihydro-4-oxo-7-fluoroquinoline-3-carboxylic acid, 1-cyclopropyl-6-fluoro-1, 4-dihydro-4-oxo-7-(4-methyl-1-piperazinyl)-quinoline-3-carboxylic acid, 1-cyclopropyl-6-fluoro-1, 4-dihydro-4-oxo-7-(4-ethyl-1-piperazinyl)-quinoline-3-carboxylic acid, 1-ethyl-6-fluoro-1, 4-dihydro-4-oxo-7-(4-methyl-1-piperazinyl)-quinoline-3-carboxylic acid, 1-ethyl-6-fluoro-1, 4-dihydro-4-oxo-7-chloroquinoline-3-carboxylic acid, 1-ethyl-6-fluoro-1, 4-dihydro-4-oxo-7-(4-ethyl-1-piperazinyl)-1, 8-naphthyridine-3-carboxylic acid and 9-fluoro-3-methyl-10-(4-methyl-1-piperazinyl)-7-oxo-2, 3-dihydro-7, 4-pyrido[1, 2, 4-de]1, 4-benzoxazine-6-carboxylic acid.Add sodium wire in portions to ethanol (2.30 g, 50 mmol) at room temperature(0.46 g, 20 mmol), heated and refluxed for 3 h.To the above solution were added dimethyl sulfoxide (15 mL), The first reaction:7-chloro-1-ethyl-6-fluoro-4-oxo-1, 4-dihydroquinoline-3-acyl chlorideA mixture of 504 mg of the above piperazine, 269 mg of
Norfloxacin intermediate.
Computed Properties
Molecular Weight:269.65
XLogP3:2.4
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:5
Rotatable Bond Count:2
Exact Mass:269.0254990
Monoisotopic Mass:269.0254990
Topological Polar Surface Area:57.6
Heavy Atom Count:18
Complexity:412
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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7-Chloro-1-ethyl-6-fluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid
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