Chemistry:Nitrafudam
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Nitrafudam is an antidepressant compound that was developed in the 1970-1980s.[1][2] It contains three functional groups: a nitrobenzene, a furan ring and an amidine.
Synthesis
Azo coupling between 2-nitrophenyldiazonium chloride [119-66-4] (1) and furfural (2) leads to 5-(2-nitrophenyl)furfural [20000-96-8] (3). Treatment of the aldehyde with hydroxylamine gives the corresponding aldoxime (PC789659). Upon dehydration, FGI to the nitrile occurs [57666-58-7] (4). A Pinner reaction with anhydrous methanolic hydrogen chloride gives the corresponding imidate (imino-ether) [62821-40-3] (5). An addition-elimination reaction with ammonia causes FGI to an amidine, thus completing the synthesis of nitrafudam (6).
References
- ↑ "5-phenyl-2-furamidines: a new chemical class of potential antidepressants". Arzneimittel-Forschung 33 (10): 1411–1416. 1983. PMID 6140016.
- ↑ Pelosi SS Jr, White RE, White RL Jr, Wright GC, You CN, US patent 3919231, issued 1975
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