Reaktion #8181

Reaktionsgleichung

3-amino-1-propanol

nitric acid

→

title compound

Ausbeute 80.0%

3-(Nitrooxy)propylamine nitric acid salt

Ausbeute 80.0%

Lösungsmittel

acetic anhydride

Reaktionsbedingungen

Aufarbeitung

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

Vorschrift

A solution of 3-amino-1-propanol (6.17 g, 82.2 mmol) was added, dropwise, to an ice-cooled solution of fuming nitric acid (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 diethyl ether (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 (DMSO-d6) δ 4.57 (br. t, 2 H), 2.8–3.0 (m, 2H), 1.96 (m, 2H). 13C NMR (DMSO-d6) δ 70.9, 36.1, 24.5. MS(API) m/z 121 (M−NO3)+.

Quelle