Synthesis Of Aceclofenac

synthesis of aceclofenac

Aceclofenac Chemical Name IUPAC : [[[2- [(2 ,6- di chloro phenyl )amino ]phenyl ]acetyl ]oxy ]acetic acid
Aceclofenac Use: non-steroidal anti-inflammatory, analgesic,antipyretic, prostaglandin synthesis inhibitor
Aceclofenac MW: 354.19 MF: C16H13Cl2NO4
Aceclofenac LD50: 121 mg/kg (M, p.o.)

A white to almost white crystalline powder. Aceclofenac M.p. 149° to 150°.
Aceclofenac solubility: It is practically insoluble in water; soluble in alcohol and methyl alcohol; freely soluble in acetone and dimethylformamide.

Thin–layer Chromatography.

Plate: silica gel. Mobile phase: chloroform:methanol:acetic acid (90:10:1). Aceclofenac, Rf 0.44; 4′-OH aceclofenac, Rf 0.25. [R. Bort et al.,Drug Metab. Dispos.,1996, 248, 834–841].

High Performance Liquid Chromatography.

System HZ—retention time 10.7 min.

Column: C₁₈ (Spherisorb ODS–2, 5 μm, 200 × 4.6 mm). Mobile phase: triethanolamine (0.02% in 100 mM phosphate buffer, pH 7.4):acetonitrile (75:25), flow rate 1.0 mL/min. UV Detection (λ=282 nm). Retention time: aceclofenac, 23.4 min; 4′-hydroxyaceclofenac, 7.6 min. [R. Bort et al.,Drug Metab. Dispos.,1996, 248, 834–841].

Reference(s):
EP 119 932 (Prodes; appl. 19.3.1984; E-prior. 21.3.1983).
US 4 548 952 (Prodes; 22.10.1985; appl. 15.3.1984; E-prior. 21.3.1983). 
Alternative synthesis:
ES 2 020 146 (Prodesfarma; appl. 29.5.1990).

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