Indoprofen

Indoprofen is a nonsteroidal anti-inflammatory drug. It was withdrawn worldwide in the 1980s after postmarketing reports of severe gastrointestinal bleeding.
A 2004 study using high-throughput screening found indoprofen to increase production of the survival of motor neuron protein, suggesting it may provide insight into treatments for spinal muscular atrophies.

Synthesis

The isoindolone ring system forms the nucleus for this profen NSAID.
The nitro group in 2-propionic acid is reduced using iron and hydrochloric acid to give 2-propionic acid. Reaction with phthalic anhydride then gives the phthalimide. Treatment with zinc in acetic acid yields indoprofen after reduction of one of the amide groups.