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Nitrafudam

Identifiers
CAS Number	64743-09-5
PubChem CID	163304
ChemSpider	143312
UNII	7R3267A08Y
ChEMBL	ChEMBL2111024
Chemical and physical data
Formula	C11H9N3O3
Molar mass	231.211 g·mol
3D model (JSmol)	Interactive image
SMILES C1=CC=C(C(=C1)C2=CC=C(O2)C(=N)N)(=O)
InChI InChI=1S/C11H9N3O3/c12-11(13)10-6-5-9(17-10)7-3-1-2-4-8(7)14(15)16/h1-6H,(H3,12,13) Key:FYUZOMGBPKUZNJ-UHFFFAOYSA-N

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 (1) and furfural (2) leads to 5-(2-nitrophenyl)furfural (3). Treatment of the aldehyde with hydroxylamine gives the corresponding aldoxime (PC789659). Upon dehydration, FGI to the nitrile occurs (4). A Pinner reaction with anhydrous methanolic hydrogen chloride gives the corresponding imidate (imino-ether) (5). An addition-elimination reaction with ammonia causes FGI to an amidine, thus completing the synthesis of nitrafudam (6).

References

1. Pong SF, Pelosi SS, Wessels FL, Yu CN, Burns RH, White RE, et al. (1983). "5-phenyl-2-furamidines: a new chemical class of potential antidepressants". Arzneimittel-Forschung. 33 (10): 1411–1416. PMID 6140016.
2. US 3919231, Pelosi SS Jr, White RE, White RL Jr, Wright GC, You CN, issued 1975, assigned to Morton Norwich Products Inc 

• Amidines
• Nitrobenzenes
• Furans
• Antidepressants