| Drug Name: | Nitrafudam |
| Width: | 250px |
| Cas Number: | 64743-09-5 |
| Pubchem: | 163304 |
| Chemspiderid: | 143312 |
| Unii: | 7R3267A08Y |
| Chembl: | 2111024 |
| C: | 11 |
| H: | 9 |
| N: | 3 |
| O: | 3 |
| Stdinchi: | 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) |
| Stdinchikey: | FYUZOMGBPKUZNJ-UHFFFAOYSA-N |
| Smiles: | C1=CC=C(C(=C1)C2=CC=C(O2)C(=N)N)[N+](=O)[O-] |
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.
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).