hydroxylamine hydrochloride; potassium carbonate in ethanol; water 1 h; Heating;

1: 99 percent / NH2OH*HCl, K2CO3 / ethanol; H2O / 1 h / Heating 2: 69 percent / pyridine / 1.) 1 h, ice cooling, 2.) 30 min, r.t. View Scheme

pyridinium p-toluenesulfonate in benzene 120 h; Heating; Yield given;

1: pyridinium p-toluenesulfonate / benzene / 120 h / Heating 2: 1) B2H6, 2) 3N NaOH, 30 percent H2O2 / 1) THF, RT, overnight, 2a) 45 deg C, 5 h, 2b) RT 3: sodium acetate, pyridinium chlorochromate / CH2Cl2 View Scheme