Reaction #985300

Reaction equation

Octyl cyanide

hydroxylamine hydrochloride

triethylamine

→

solid

Yield 27.0%

N-Hydroxy-nonanamidine

Yield 27.0%

Solvents

EtOH

Conditions

Workup

1. 1
   Temperatureat reflux over night
2. 2
   ExtractionExtraction

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).

Source