HCID 19979377, compound → 6-Chloro-2,4-bis(1-methylethyl)-3-pyridinamine

Reaction equation

[Cl:1][C:2]1[N:7]=[C:6]([CH:8]([CH3:10])[CH3:9])[C:5]([N+:11]([O-])=O)=[C:4]([CH:14]([CH3:16])[CH3:15])[CH:3]=1.[H][H]>O1CCCC1.[Ni]>[Cl:1][C:2]1[N:7]=[C:6]([CH:8]([CH3:9])[CH3:10])[C:5]([NH2:11])=[C:4]([CH:14]([CH3:16])[CH3:15])[CH:3]=1

Participants

Procedure

30.0 g of 6-chloro-2,4-diisopropyl-3-nitropyridine are dissolved in 450 ml of tetrahydrofuran and, after the addition of 30.0 g of Raney nickel (suspended in ethanol), hydrogenated under a hydrogen pressure of 20 bar at from +30° C. to +35° C. The reaction mixture is filtered over diatomaceous earth and the filtrate is concentrated. The residue is purified by column chromatography on silica gel (eluant: ethyl acetate/hexane 3). 6-Chloro-2,4-diisopropyl-3-aminopyridine is obtained in the form of a clear crystalline powder, m.p. 53°-56° C.