Reacción #8181

Ecuación de reacción

3-amino-1-propanol

nitric acid

→

title compound

Rendimiento 80.0%

3-(Nitrooxy)propylamine nitric acid salt

Rendimiento 80.0%

Disolventes

acetic anhydride

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.WAITat room temperature for 10 minutes
2. 2
   OtroThe 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
   Otroprecipitated
5. 5
   FiltraciónThe mixture was filtered
6. 6
   Otrothe white crystalline solid was dried in vacuo

Procedimiento

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)+.

Fuente