Nitric Acid → 3-Nitroxypropylamine nitrate

Participants

Reaction Steps

A solution of 3-amino-1-propanol (6.17 g, 82.2 mmol) was added, drop-wise, to an ice-cooled solution of fuming nitric acid (90%, 12 mL) in acetic anhydride (50 mL). The reaction was stirred in an ice-bath for 10 minutes and then at room temperature for 10 minutes. The solvent was evaporated under vacuum at 40° C. The residue was stirred in diethylether (200 mL) until the product precipitated. The mixture was filtered and the white crystalline solid was dried in vacuo to give the title compound (12.1 g, 80% yield). 1H NMR (300 MHz, DMSO-d6) δ 4.57 (br. t, 2H), 2.8-3.0 (m, 2H), 1.98-1.93 (m, 2H). 13C NMR (75 MHz, DMSO-d6) δ 70.9, 36.1, 24.5. MS m/z 121 (M−NO3)+.

Provenance & Evidence