Ethanolamine → 2-(Nitrooxy)ethan-1-aminium nitrate

Temperature

0 °C

2-Hydroxyethylamine (5 g, 81.9 mmol) in EtOAc (40 mL) was added drop-wise to a mixture of fuming HNO3 (18 g, 12 mL, 0.29 mol) and Ac2O (54 g, 50 mL, 0.53 mol) at −10° C. The reaction mixture was stirred at 0° C. for 10 minutes and at room temperature for 10 minutes. The solvent was evaporated in high vacuo at 40° C. The residue was sonicated with ether. The solid was filtered and washed with hexane to give the title compound as a white solid. Mp 92-94° C. 1H NMR (300 MHz, d6-DMSO) δ 7.71-8.25 (bs, 3H), 4.72 (t, J=5.0 Hz, 2H), 3.23 (d, J=5.0 Hz, 2H). 13C NMR (75 MHz, d6-DMSO) δ 70.9, 37.4.

1. customThe solvent was evaporated in high vacuo at 40° C
2. customThe residue was sonicated with ether
3. filtrationThe solid was filtered
4. washwashed with hexane

ORD record

ord-05e06035ee114d34b098849a176ca7aa

Source dataset

uspto-grants-2012_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08222277B2