hydroxylamine in ethanol reflux for 2.5 h then 0 deg C overnight;

hydroxylamine hydrochloride; sodium methylate in methanol 1)room temp., overnight 2)autoclave, 120 deg C, 7h;

1: 90 percent / thionyl chloride, DMF / CHCl3 / 4 h / Heating 2: 75 percent / hydrxylamine hydrochloride, sodium methoxide / methanol / 1)room temp., overnight 2)autoclave, 120 deg C, 7h View Scheme

1: 92 percent / 3-methylbutylnitrite / acetic acid; H2O / 48 h / Ambient temperature 2: 84 percent / dimethylaminopyridine / stirred overnight 3: 90 percent / thionyl chloride, DMF / CHCl3 / 4 h / Heating 4: 75 percent / hydrxylamine hydrochloride, sodium methoxide / methanol / 1)room temp., overnight 2)autoclave, 120 deg C, 7h View Scheme

1: 84 percent / dimethylaminopyridine / stirred overnight 2: 90 percent / thionyl chloride, DMF / CHCl3 / 4 h / Heating 3: 75 percent / hydrxylamine hydrochloride, sodium methoxide / methanol / 1)room temp., overnight 2)autoclave, 120 deg C, 7h View Scheme