Nitric Acid → 3-Nitroxypropylamine nitrate

HRID 8085

Reaction equation

HRID 8085 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-fd95e3c9024b41f58c60e5039c57717d
Source dataset
uspto-grants-2006_08
Patent number
US07087630B2

Linked notes

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