4-Amino-3-nitrobenzonitrile → HCID 21272872, compound

Participants

Reaction Steps

One equivalent of diborane in THF was added to a solution of 1-amino-2-nitro-4-cyanobenzene (500 mg.) in anhydrous THF (20 ml.) under nitrogen at 10°. After 2 hours excess diborane was destroyed by addition of MeOH and the reaction mixture was evaporated to dryness. The residue was dissolved in methanol and methanolic HCl added. The solvent was evaporated, the residue was basified and the product extracted with ether (x3). The combined extracts were dried and evaporated to give impure 1-amino-2-nitro-4-aminomethylbenzene. To a solution of this diamine (350 mg.) in dry dioxan (10 ml.) was added "Boc-On" (Aldrich Chemical Co.) (258 mg.). The reaction mixture was stirred at ambient temperature for 18 hours, concentrated, and the residue purified by chromatography on silica using CH2Cl2 /ether as eluant. There was thus obtained 1-amino-2-nitro-4-(t-butoxycarbonylaminomethyl)benzene. This product was hydrogenated at ambient pressure in THF/ethanol solution using 10% w/w palladium-on-carbon catalyst to give 1,2-diamino-4-(t-butoxycarbonylaminomethyl)benzene which was used without further purification.

Provenance & Evidence