Nitric Acid → 3-Nitroxypropylamine nitrate

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)+.

1. waitat room temperature for 10 minutes
2. customThe solvent was evaporated under vacuum at 40° C
3. stirringThe residue was stirred in diethylether (200 mL) until the product
4. customprecipitated
5. filtrationThe mixture was filtered
6. customthe white crystalline solid was dried in vacuo

ORD record

ord-237f7a1b7c7b42ef84c6be7b397488e5

Source dataset

uspto-grants-2011_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07883714B2