4-Aminobenzonitrile → HCID 178507471, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 4-amino-benzonitrile (300 mg, 2.53 mmol; CAS Reg. No. 873-74-5) in dry DMF (6 ml) was added NH4Cl (547 mg, 10.2 mmol) and NaN3 (660 mg, 10.2 mmol) at room temperature. The reaction mixture was then heated at 120° C. for 12 h. After cooling, TLC shows formation of new spot, filtered the solid material by sintered funnel and washed the solid residue by EtOAc (4×5 ml). Combined organic layers were reduced under pressure at 60° C. and diluted the residue with EtOAc (25 mL). Organic layer was washed with H2O (15 ml), brine (12 ml) and dried over Na2SO4; which was then concentrated under reduced pressure to give the crude material (300 mg). Crude product was then purified by column chromatography [SiO2 (230-400 mesh), MeOH:DCM 5:95] to give the title compound (180 mg, 44.4%) as light yellow solid.

Provenance & Evidence