Triethylamine → N'-hydroxynonanimidamide

HRID 898118

Reaction equation

HRID 898118 reaction equation
[CH2:1]([C:9]#[N:10])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].Cl.[NH2:12][OH:13].C(N(CC)CC)C>CCO>[OH:13][NH:12][C:9](=[NH:10])[CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 16715NonanenitrileHCID 443297Hydroxyamine hydrochloride

Product 1

HCID 5074022N'-hydroxynonanimidamideYield 27%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Octyl cyanide (2 g, 14 mmol) and hydroxylamine hydrochloride (2.495 g, 36 mmol) were dissolved in EtOH (10 mL) and treated with triethylamine (5 mL, 36 mmol) at reflux over night. Extraction: AcOEt/water. Silica gel chromatography: heptane/AcOEt 1:2 afforded a white solid (0.65 g, 26%). MS: m/z=173 (M +H).

Workup

  1. temperatureat reflux over night
  2. extractionExtraction

Sources & evidence

ORD record
ord-344e2ede1a55402092f36b2c52f6ed11
Source dataset
uspto-grants-2008_04
Patent number
US07351700B2

Linked notes

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