Adapalene Study On Synthesis

Acne is a common dermatogic disease with a morbidity rate of 85% in the world. It affects mostly the people between the ages of 12 and 24. It is related to abnormal keratinisation by excessive sebum secretion,Adapalene is a retinoid agent for the treatment of local acne. It can be used alone for the mild acne or in combination with antimicrobials for inflammatory acne. It has been proved efficacious as maintenance treatment. Adapalene has become the first-line medication for acne.Based on the literatures, the synthetic route of Adapalene was designed and studied. It was synthesized with the starting material 4-bromophenol via Friedel-Crafts reaction, methylation, Grignard reaction, coupling reaction and hydrolyzation with an overall yield of 67.8%. The structure of target compound was identified by IR, ~1H-NMR and ESI-MS.The synthesis of the important intermediate, methyl 6-bromo-2-naphthoate, was also studied. It was synthesized with 2-bromonaphthalene via acetylation and hydrolyzation. The structure of the intermediate was identified by ~1H-NMR and ESI-MS.Due to the simple operation, the route of Adapalene is easy to scale-up for industrial use.