Sodium Hydroxide → 3,5-Diaminobenzonitrile
Reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:9]=[C:10]([N+:12]([O-])=O)[CH:11]=1)[C:7]#[N:8])([O-])=O.Cl[Sn]Cl.[OH-].[Na+]>Cl>[NH2:1][C:4]1[CH:5]=[C:6]([CH:9]=[C:10]([NH2:12])[CH:11]=1)[C:7]#[N:8]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
To 3,5-dinitrobenzonitrile (5.0 g, 25.89 mmol) in 20 mL of HCl 1M, was added SnCl2 (34.4 g, 7 eq). The reaction mixture was stirred at room temperature for 2 h and then cooled to 0° C. The mixture was made alkaline with a 50% aqueous solution of NaOH and the precipitate was removed by filtration. The filtrate was extracted with ethyl acetate and the combined organic layers were evaporated. The residue and the precipitate were purified by flash chromatography on silica gel (DCM/MeOH//95/5) to yield expected compound as an orange solid (1.95 g, 57% yield). m/z (ESI) 134.0 [M+H]+.