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

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Reaction Steps

A mixture of 0.312 g (1.87 mmol) of the above nitro compound and 0.205 g of 10% Pd/C in methanol (40 mL) was stirred under hydrogen (25 in/Hg) for 5 hrs. The reaction mixture was filtered through celite, and the solvent was concentrated, to give 0.236 g (92% yield) of N2,N2-dimethyl-2,5-pyridinediamine: 1H NMR (CDCl3) δ7.78 (d, J=2.9 Hz, 1H), 6.98 (dd, J=8.8, 2.9 Hz, 1H), 6.45 (dd, J=8.8, 0.5 Hz, 1H), 2.99 (s, 6H); LCMS (APCI+) m/z: 138 (MH+, 100%).

Provenance & Evidence