Meclofenamic acid

Meclofenamic acid Basic information
Product Name:Meclofenamic acid
Synonyms:2-(2,6-dichloro-3-methyl-anilino)benzoic acid;Meclofenamic acid Solution, 100ppm;Arquel;INF 4668;N-(2,6-Dichloro-m-tolyl)anthranilic Acid;N-(3-Methyl-2,6-dichlorophenyl)anthranilic Acid;NSC 95309;Meclofen
CAS:644-62-2
MF:C14H11Cl2NO2
MW:296.15
EINECS:2114195
Product Categories:Aromatics;Intermediates & Fine Chemicals;Pharmaceuticals
Mol File:644-62-2.mol
Meclofenamic acid Structure
Meclofenamic acid Chemical Properties
Melting point 257-259°C
Boiling point 399.4±42.0 °C(Predicted)
density 1.3567 (rough estimate)
refractive index 1.6070 (estimate)
storage temp. Refrigerator
solubility Chloroform (Slightly), Methanol (Slightly, Heated)
pkapKa 4.0 (Uncertain)
form Solid
color Off-White to Light Orange
EPA Substance Registry SystemBenzoic acid, 2-[(2,6-dichloro-3-methylphenyl)amino]- (644-62-2)
Safety Information
MSDS Information
Meclofenamic acid Usage And Synthesis
Chemical PropertiesWhite Crystalline Solid
OriginatorMeclomen,Warner Lambert,US,1980
UsesMeclofenamic acid is used for the same conditions as flufenamic acid.
UsesAnti-inflammatory; antipyretic
DefinitionChEBI: An aminobenzoic acid that is anthranilic acid in which one of the hydrogens attached to the nitrogen is replaced by a 2,6-dichloro-3-methylphenyl group. A non-steroidal anti-inflammatory drug, it is used as the sodium salt for the treatment of dysmenorrhoe (painful periods), osteoarthritis and rheumatoid arthritis.
Manufacturing ProcessA mixture consisting of 22.7 g potassium o-bromobenzoate, 16.6 g 2,6- dichloro-3-methylaniline, 12 ml N-ethylmorpholine, 60 ml diethylene glycol dimethyl ether, and 1.0 g anhydrous cupric bromide is heated in a nitrogen atmosphere at 145°C to 155°C for 2 hours. The reaction mixture is diluted with 60 ml diethylene glycol dimethyl ether and acidified with 25 ml concentrated hydrochloric acid. The acidic mixture is diluted with 100 ml of water and the liquid phase decanted from the insoluble oil. The insoluble oil is stirred with methanol and the crystalline N-(2,6-dichloro-3-methylphenyl) anthranilic acid which separates is collected and washed with methanol. The product, after recrystallization from acetone-water mixture, melts at 248°C to 250°C.
Brand nameMeclomen (Parke-Davis).
Therapeutic FunctionAntiinflammatory
SynthesisMeclofenamic acid, N-(2,6-dichloro-m-tolyl)anthranylic acid (3.2.20), is synthesized analogous to flufenamic acid, by the reaction of potassium salt of 2-bromobenzoic acid with 2,6-dichloro-3-methylaniline in the presence of copper (II) bromide in a mixture of N-ethylmorpholine and diglyme [82,83].

Synthesis_644-62-2

Meclofenamic acid Preparation Products And Raw materials
Raw materials2-Chlorobenzoic acid-->4-Chloro-3-nitrotoluene-->N-Ethylmorpholine-->2,6-Dichloro-3-methylaniline
Hyaluronic acid Ethyl 2-(Chlorosulfonyl)acetate AQUANTRAAL 3,5-Dichlorobenzoic acid CLOFENAMIC ACID m-Toluic acid 4-Dimethylaminobenzoic acid 4-Aminobenzoic acid Stearic acid Folic acid Glycine terofenamate Tolfenamic acid Meclofenamic acid MonoclofenamicAcid Anthranilic acid BENZOICACID Citric acid

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