hydroxylamine hydrochloride in pyridine; acetic anhydride T=100°C;

pyridine; 2,4,6-trichloro-1,3,5-triazine in dichloromethane 1.5 h; Heating;

1: bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; piperidine / N,N-dimethyl-formamide / 60 °C / |Inert atmosphere 2: manganese(IV) oxide / dichloromethane / |Sonication; |Inert atmosphere 3: hydroxylamine hydrochloride / pyridine; acetic anhydride / 100 °C View Scheme

2: 91 percent / hydroxylamine hydrochloride, K2CO3 / aq. ethanol / 2 h / Ambient temperature 3: 64 percent / 2,4,6-trichloro-s-triazine, pyridine / CH2Cl2 / 1.5 h / Heating View Scheme

potassium hydroxide in ethanol 2 h; Heating;