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 Synthetic Method of Carprofen
  • Synthetic Method of Carprofen
  • (CAS NO.: ), with its systematic name of 6-Chloro-alpha-methylcarbazole-2-acetic acid, could be produced through many synthetic methods.

    Following is one of the synthesis routes:

    Systematic Method of Carprofen

    Firstly, Cyclohexenone (I) could be condensed with diethyl alpha-methylmalonate (II) in the presence of sodium ethoxide in ethanol to produce diethyl alpha-methyl-3-oxocyclohexanemalonate (III), oil b.p.(0.8) = 149-52 C, n(20)(D) = 1.4660, which is hydrolyzed and decarboxylated with refluxing dioxane-HCl to yield alpha-methyl-3-oxocyclohexaneacetic acid (IV), oil, b.p.(0.7) = 164-6 C, n(20)(D) = 1.4794. Next, compound (IV) is condensed with 4-chlorophenylhydrazine (A) in acetic acid-water to give 6-chloro-alpha-methyl-1,2,3,4-tetrahydrocarbazole-2-acetic acid (V) with m.p. 193-202 C, and then the yielding product is esterified with ethanol-HCl to ethyl 6-chloro-alpha-methyl-1,2,3,4-tetrahydrocarbazole-2-acetate (VI) and aromatized with chloranil (B) in refluxing xylene to produce ethyl 6-chloro-alpha-methylcarbazole-2-acetate (VII) with m.p. 106.0-7.5 C. At last, this ester is hydrolyzed with NaOH in refluxing ethanol.


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