Reaction #502112

Reaction equation

3-amino-1-propanol

nitric acid

→

title compound

Yield 80.0%

3-(Nitrooxy)propylamine nitric acid salt

Yield 80.0%

Solvents

acetic anhydride

Conditions

Workup

1. 1
   workup.WAITat room temperature for 10 minutes
2. 2
   OtherThe solvent was evaporated under vacuum at 40° C
3. 3
   workup.STIRRINGThe residue was stirred in diethylether (200 mL) until the product
4. 4
   Otherprecipitated
5. 5
   FiltrationThe mixture was filtered
6. 6
   Otherthe white crystalline solid was dried in vacuo

Procedure

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)+.

Source