Hydroxyamine hydrochloride → 5-Methyl-6-methylthio-3-pyridinecarboxamide

Participants

Reaction Steps

To a stirred s odiu m methoxide solution (25 wt % in methanol; 10.53 g, 48.7 mmol) diluted in dry methanol (100 mL) at room temperature under a nitrogen atmosphere was added hydroxylamine hydrochloride (3.38 g, 48.7 mmol) and 5-methyl-6-methylthio-3-pyridinecarbonitrile (2.00 g, 12.2 mmol). The white suspension was stirred at room temperature for 7 days, when it was evaporated in vacuo. The crude white solid was chromatographed on silica gel (25% EtOAc/pentane) yielding the desired product (1.66 g, 75%) as a white fluffy powder.

Provenance & Evidence