Nitrafudam


Nitrafudam is an antidepressant compound that was developed in the 1970-1980s. It contains three functional groups: a nitrobenzene, a furan ring and an amidine.

Synthesis

Azo coupling between 2-nitrophenyldiazonium chloride and furfural leads to 5-furfural . Treatment of the aldehyde with hydroxylamine gives the corresponding aldoxime. Upon dehydration, FGI to the nitrile occurs . A Pinner reaction with anhydrous methanolic hydrogen chloride gives the corresponding imidate . An addition-elimination reaction with ammonia causes FGI to an amidine, thus completing the synthesis of nitrafudam.