Highly Convenient, One-Pot Synthesis of Nitriles from Aldehydes Using the NH₂OH·HCl/NaI/MeCN System

Ballini Roberto. Fiorino Dennis . Palmieri Alessandro. Synlett  2003,  1841 

The authors have found that the reported procedure for the conversion of aromatic aldehydes into nitriles leads to poorly reproducible results. The new procedure involves the utilization of DMF as solvent and 4 equivalents of NaI at reflux. The general method for conversion of aromatic aldehydes and the corrected yields of the obtained nitriles follow.

General Procedure for the One-Pot Preparation of Aryl Nitriles

To a stirred heterogeneous mixture of NH₂OH·HCl (1.3 mmol) and NaI (4 mmol) in DMF (4 mL), aldehyde 1 (1 mmol) was added at room temperature. The reaction mixture was refluxed for 6 h, then was allowed to cool and was poured into cold 1N HCl (10 mL). After extraction with Et₂O (3 ¥ 10 mL), the combined organic layers were dried (Na₂SO₄), filtered, and concentrated under vacuum. The crude nitrile was purified by flash chromatography to give the pure ­compound 2. []