Synthesis of Indomethacin

IUPAC Name

2-{1-[(4-Chlorophenyl)carbonyl]-5-methoxy-2-methyl-1H-indol-3-yl}acetic acid
Trade Name: Indocin

Biosynthesis of Indomethacin

Indomethacin can be synthesized from p-anisidine. Diazotization of p-anisidine followed by reduction yield p-methoxy phenyl hydrazine which undergoes Fischer-Indole synthesis in the presence of methyl levulinate to form a hydrazone which on intramolecular rearrangement gives an enamine.Further on cyclization losses a molecule of ammonia and forms an intermediate which on hydrolyzed followed by esterification to give tert-butyl ester. Finally acylation with p-chlorobenzoyl chloride followed by debutylation gives rise to the required product Indomethacin.

Therapeutic Uses of Indomethacin

Indomethacin can be used in the treatment of following diseases-
Osteoarthritis
Rheumatoid arthritis
Gouty arthritis
Ankylosing spondylitis
Shoulder pain caused by bursitis or tendinitis