Hydrochloric Acid → N2-(2-(dimethylamino)ethyl)pyridine-2,5-diamine

Beteiligte Stoffe

Reaktionsbedingungen

Reaktionsschritte

To a round bottom flask, charged with N1,N1-dimethyl-N2-(5-nitropyridin-2-yl)ethane-1,2-diamine (0.4 g, 1.90 mmol) from above, 5 mL of ethanol, 5 mL water followed by iron powder (0.416 g, 7.58 mmol) and ammonium chloride (0.402 g, 7.58 mmol). The resulting reaction mixture was heated at 80° C. for 3 hours. TLC analysis showed no acid remaining so the mixture was passed through a cellite cartridge to remove iron. The organic solution was concentrated under vacuo to give a brown oil residue. The resulting crude mixture was treated with hydrochloric acid (1 N) and washed with ethylacetate. The aqueous layer was basified to PH=10 using sodium carbonate and extracted with ethyl acetate and washed with brine and water. The organic layer was separated, dried (Na2SO4) and concentrated. The title product was obtained as a brown solid (0.23 g, 51% yield). MS m/z: 181.16 [M+H]+.

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