Ethylenediamine → 4-chloro-2-(4,5-dihydro-1H-imidazol-2-yl)pyridine

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([C:8]#[N:9])[CH:3]=1.C[O-].[Na+].[CH2:13](N)[CH2:14][NH2:15]>CO>[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([C:8]2[NH:15][CH2:14][CH2:13][N:9]=2)[CH:3]=1

Participants

Procedure

To a solution of 4-chloropyridine-2-carbonitrile (20.0 g, 121 mmol, prepared as described by Sakamoto et al. Chem. Pharm. Bull. 1985, 33, 565-571) in MeOH (240 mL), was added sodium methoxide (0.655 g, 12.1 mmol). The reaction mixture was stirred at rt under an atmosphere of argon for 2 h. Ethylene diamine (40.0 mL, 597 mmol) was added to the reaction mixture was stirred at 50° C. for 20 h. The solution was allowed to cool to rt and concentrated. The residue was partitioned between water and DCM. The organic layer was separated, dried over MgSO4, filtered and concentrated to give the desired product as a light brown solid (21.9 g, >99%). LCMS: (FA) ES+ 182.09 (M+1).