Nitric Acid → 3-Nitroxypropylamine nitrate

HRID 1873618Notes

Reaction equation

HRID 1873618 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][OH:5].[N+:6]([O-:9])([OH:8])=[O:7]>C(OC(=O)C)(=O)C>[N+:6]([O-:9])([OH:8])=[O:7].[N+:6]([O:5][CH2:4][CH2:3][CH2:2][NH2:1])([O-:8])=[O:7]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 90863-Amino-1-propanol

Product 1

HCID 220145913-Nitroxypropylamine nitrateYield 80%

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

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)+.

Workup

  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

Sources & evidence

ORD record
ord-09161e14b8c548f39a049f10a260055a
Source dataset
uspto-grants-2012_11
Patent number
US08304409B2

Reaction notes

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