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

反応式

[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

参加物

実験手順

To a solution of 4-chloropyridine-2-carbonitrile (20.0 g, 121 nmuol, prepared as described by Sakamoto et al. Chem. Pharm. Bull. 1985, 33, 565-71) in MeOH (240 mL), was added sodium methoxide (0.655 g, 12.1 mmol). The reaction mixture was allowed to stir at rt under an atmosphere of argon for 2 h. Ethylene diamine (40.0 mL, 597 imol) was added and the mixture was allowed to stir at 50° C. for 20 h. The reaction mixture was allowed to cool to rt and then concentrated. The residue was dissolved in a mixture of water and DCM. The organic layer was separated, dried over MgSO4, filtered and concentrated to give 4-chloro-2-(4,5-dihydro-1H-imidazol-2-yl)pyridine as a light brown solid (21.9 g, >99%). LCMS: (FA) ES+ 182.1.