1-ETHYL-7-CHLORO-6-FLUORO-1,4-DIHYDRO-4-OXOQUINOLINE-3-CARBOXYLIC ACID Chemical Properties

Melting point:

245°C

Boiling point:

437.9±45.0 °C(Predicted)

Density 

1.3905 (estimate)

storage temp. 

Sealed in dry,2-8°C

solubility 

DMSO (Slightly, Heated), Methanol (Slightly, Heated)

form 

powder

pka

-0.21±0.20(Predicted)

color 

White to Pale Yellow

InChIKey

WNNSMMJBBOPPOT-UHFFFAOYSA-N

CAS DataBase Reference

68077-26-9(CAS DataBase Reference)

Safety Information

Risk Statements 

52/53

Safety Statements 

61

HazardClass 

IRRITANT

HS Code 

2933599550

MSDS

• Language:English Provider:ACROS
• Language:English Provider:ALFA

1-ETHYL-7-CHLORO-6-FLUORO-1,4-DIHYDRO-4-OXOQUINOLINE-3-CARBOXYLIC ACID Usage And Synthesis

Chemical Properties

White powder

Uses

7-Chloro-1-ethyl-6-fluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic Acid (Norfloxacin EP Impurity A) is a Norfloxacin intermediate. Norfloxacin EP Impurity A; Norfloxacin USP Related Compound A (7-Chloro-1-ethyl-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic Acid).

Synthesis

Ethyl 7-chloro-1-ethyl-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylate (2.75 g, 9.24 mmol) was used as a raw material and dissolved in 60 mL of methanol. Subsequently, a 1:1 solution of hydrochloric acid (31.5 mL, 189 mmol) was added. The reaction mixture was heated to reflux for 2 h. Upon completion of the reaction, a white solid precipitated. The solid product was collected by filtration and washed with plenty of water. Finally, the product was dried in a vacuum oven for 2 h to afford 7-chloro-1-ethyl-6-fluoro-1,4-dihydro-4-carbonylquinoline-3-carboxylic acid (2.46 g, yield: 89.5%).

References

[1] Journal of Medicinal Chemistry, 2009, vol. 52, # 14, p. 4257 - 4265
[2] Liebigs Annalen der Chemie, 1987, p. 29 - 37
[3] Chemical Communications, 2018, vol. 54, # 15, p. 1869 - 1872
[4] Journal of Medicinal Chemistry, 1980, vol. 23, # 12, p. 1358 - 1363
[5] Patent: CN107445892, 2017, A. Location in patent: Paragraph 0016

1-ETHYL-7-CHLORO-6-FLUORO-1,4-DIHYDRO-4-OXOQUINOLINE-3-CARBOXYLIC ACID(68077-26-9)Related Product Information

• Norfloxacin
• Norfloxacin Impurity 2
• 6-Chloro-1-Ethyl-4-Oxo-7-(Piperazin-1-yl)-1,4-Dihydroquinoline-3-Carboxylic acid
• Desethylene Norfloxacin Hydrochloride
• Norfloxacin EP Impurity E
• Norfloxacin EP Impurity H
• 6-Fluoro-1,4-dihydro-1-methyl-4-oxo-7-(1-piperazinyl)-3-quinolinecarboxylic acid
• Norfloxacin EP Impurity D
• Norfloxacin EP Impurity G
• Norfloxacin EP Impurity C
• 4-OXO-1,4-DIHYDROQUINOLINE-3-CARBOXYLIC ACID
• 3-Quinolinecarboxylic acid
• 7-Chloro-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid
• 1-ETHYL-7-CHLORO-6-FLUORO-1,4-DIHYDRO-4-OXOQUINOLINE-3-CARBOXYLIC ACID
• 7-CHLORO-1-CYCLOPROPYL-6-FLUORO-4-OXO-1,4-DIHYDRO-QUINOLINE-3-CARBOXYLIC ACID ETHYL ESTER
• METHYL 7-CHLORO-6-FLUORO-1-CYCLOPROPYL-1,4-DIHYDROGEN-4-OXO-3-QUINOLINE CARBOXYLATE
• AKOS 92521
• AKOS 1306