tert-Butyl (5-nitropyridin-2-yl)carbamate → tert-butyl N-(5-aminopyridin-2-yl)carbamate

Participants

Reaction Steps

A mixture of tert-butyl 5-nitropyridin-2-ylcarbamate (3.76 g, 15.7 mmol) and Pd/C (Aldrich) (0.588 g, 5.52 mmol) in EtOH (100 mL) was evacuated under vacuum and refilled with hydrogen (6 times). The mixture was hydrogenated under balloon pressure of hydrogen at rt for 2.5 h. The reaction mixture was filtered through a pad of Celite® (diatomaceous earth) (eluent:EtOH) and concentrated to give tert-butyl 5-aminopyridin-2-ylcarbamate (3.22 g, 98% yield) as a cream color solid. 1H NMR (300 MHz, d6-DMSO) δ 9.06 (s, 1H); 7.62 (d, J=1.75 Hz, 1H); 7.40 (d, J=8.62 Hz, 1H); 6.94 (dd, J=8.70, 2.27 Hz, 1H); 4.93 (s, 2H); 1.44 (s, 9H). m/z (ESI, +ve ion) 210.2 (M+H)+.

Provenance & Evidence