1-Cyclopropyl-6,7-difluoro-1,4-dihydro-8-hydroxy-4-oxo-3-quinolinecarboxylic Acid

1-Cyclopropyl-6,7-difluoro-1,4-dihydro-8-hydroxy-4-oxo-3-quinolinecarboxylic Acid Property

Melting point:

>271oC (dec.)

Boiling point:

478.3±45.0 °C(Predicted)

Density 

1.745±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

solubility 

DMSO (Slightly), Methanol (Slightly, Heated)

pka

5.75±0.20(Predicted)

form 

Solid

color 

White to Pale Beige

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H332Harmful if inhaled

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

1-Cyclopropyl-6,7-difluoro-1,4-dihydro-8-hydroxy-4-oxo-3-quinolinecarboxylic Acid Chemical Properties,Usage,Production

Uses

Moxifloxacin (M745000) impurity.

Synthesis

About 500 mL of DMSO filtrate from the nucleophilic substitution reaction was transferred to a 1000 mL reactor and anhydrous calcium chloride (about 33 g) was added under stirring conditions. The reaction mixture was cooled with stirring to 0-5 °C and maintained in this temperature range for 30 minutes. Subsequently, the pH was adjusted to 4 with a 15% aqueous hydrochloric acid solution, the temperature was maintained between 0-5°C, and stirring was continued for 3 hours. Upon completion of the reaction, the precipitated product was collected by filtration, washed well with acetone and then dried. A dry 1-cyclopropyl-6,7-difluoro-8-hydroxy-4-oxo-1,4-dihydroquinoline-3-carboxylic acid (about 35 g) with a purity of more than 90% was finally obtained.

References

[1] Patent: WO2006/4561, 2006, A1. Location in patent: Page/Page column title page; 4; 12-13
[2] Patent: WO2008/62379, 2008, A2. Location in patent: Page/Page column 37
[3] Patent: US2010/222302, 2010, A1. Location in patent: Page/Page column 21
[4] Patent: WO2007/17828, 2007, A2. Location in patent: Page/Page column 54