Nitric Acid → 3-Nitroxypropylamine nitrate

HRID 2117974Notes

Reaction equation

HRID 2117974 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, 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)+.

Workup

  1. waitat room temperature for 10 minutes
  2. customThe solvent was evaporated under vacuum at 40° C
  3. stirringThe residue was stirred in diethyl ether (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-cf21f18bed6c4fb887eb937fd853f1cc
Source dataset
uspto-grants-2008_10
Patent number
US07442802B2

Reaction notes

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