|
|
| | 1-ETHYL-7-CHLORO-6-FLUORO-1,4-DIHYDRO-4-OXOQUINOLINE-3-CARBOXYLIC ACID Basic information |
| | 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) | | pka | -0.21±0.20(Predicted) | | form | powder | | color | White to Pale Yellow | | Major Application | pharmaceutical (small molecule) | | InChI | 1S/C12H9ClFNO3/c1-2-15-5-7(12(17)18)11(16)6-3-9(14)8(13)4-10(6)15/h3-5H,2H2,1H3,(H,17,18)/p-1 | | InChIKey | WNNSMMJBBOPPOT-UHFFFAOYSA-N | | SMILES | Fc1cc2c(cc1Cl)N(C=C(C2=O)C(=O)[O-])CC | | CAS DataBase Reference | 68077-26-9(CAS DataBase Reference) |
| Risk Statements | 52/53 | | Safety Statements | 61 | | HazardClass | IRRITANT | | HS Code | 2933599550 |
| | 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 Preparation Products And Raw materials |
|