Reaction #502120

Reaction equation

2-Hydroxyethylamine

HNO3

Ac2O

→

title compound

2-(Nitrooxy)ethylammonium nitrate

Solvents

EtOAc

Conditions

Workup

1. 1
   OtherThe solvent was evaporated in high vacuo at 40° C
2. 2
   OtherThe residue was sonicated with ether
3. 3
   FiltrationThe solid was filtered
4. 4
   Washwashed with hexane

Procedure

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.

Source