N,N-dimethyl-5-nitropyridin-2-amine → N2,N2-dimethylpyridine-2,5-diamine

Participants

Reaction Conditions

Reaction Steps

A stirred mixture of the product from Step 1 (7.70 g, 0.0461 mol) and stannous chloride dihydrate (56.4 g, 0.250 mol) in absolute EtOH (100 ml) was warmed to 80° C. during 15 minutes and kept at that temperature for 35 minutes. The resulting mixture was kept at ambient temperature for 1 hour, poured onto ice (400 ml) and mixed with NaHCO3 (15 g). It was adjusted to a pH of 8-9 with saturated aqueous NaHCO3 and extracted with EtOAc; the extract was washed with water and brine dried (MgSO4) and concentrated to give 5.98 g of crude product. Pan of this was purified by silica gel chromatography, with 5% MeOH--0.25% NH4OH--CHCl3 to give the titled product.

Provenance & Evidence