sodium methylate

hydroxylamine hydrochloride; sodium methylate 1.) glacial acetic acid, reflux, 15 min, 2.) diethyl ether, MeOH; Yield given. Multistep reaction. Yields of byproduct given;

1: 1.) hydroxylamine hydrochloride, 2.) sodium methylate / 1.) glacial acetic acid, reflux, 15 min, 2.) diethyl ether, MeOH 2: 89 percent / NaOMe / methanol View Scheme

pyridine

1: 1.) hydroxylamine hydrochloride, 2.) sodium methylate / 1.) glacial acetic acid, reflux, 15 min, 2.) diethyl ether, MeOH 2: 89 percent / NaOMe / methanol 3: 92 percent / HCl gas / 16 h / -5 °C 4: 77 percent / AcOH, conc. HCl, water / 7 h / Heating 5: Michael condensation 6: 20percent aq. KOH View Scheme