in toluene

hydrogenchloride 1.5 h; Heating;

sodium hydroxide; hydroxylamine hydrochloride in ethanol 1.5 h; Heating;

1: SOCl2 / 2 h / Heating 2: 2 h / Heating 3: 1.) LDA / 1.) THF, n-heptane, -78 deg C, 0.5 h, 2.) THF, n-heptane, a) -78 deg C, 0.5 h, b) from -78 deg C to RT, 2 h, c) RT, overnight 4: 1.) LDA / 1.) THF, -78 deg C, 0.5 h, 2.) THF, a) -78 deg C, 0.5 h, b) from -78 deg C to RT, 2 h, c) RT, 13 h 5: NH2OH*HCl, aq. NaOH / ethanol / 1.5 h / Heating View Scheme

1: 2 h / Heating 2: 1.) LDA / 1.) THF, n-heptane, -78 deg C, 0.5 h, 2.) THF, n-heptane, a) -78 deg C, 0.5 h, b) from -78 deg C to RT, 2 h, c) RT, overnight 3: 1.) LDA / 1.) THF, -78 deg C, 0.5 h, 2.) THF, a) -78 deg C, 0.5 h, b) from -78 deg C to RT, 2 h, c) RT, 13 h 4: NH2OH*HCl, aq. NaOH / ethanol / 1.5 h / Heating View Scheme

1: 1.) LDA / 1.) THF, n-heptane, -78 deg C, 0.5 h, 2.) THF, n-heptane, a) -78 deg C, 0.5 h, b) from -78 deg C to RT, 2 h, c) RT, overnight 2: 1.) LDA / 1.) THF, -78 deg C, 0.5 h, 2.) THF, a) -78 deg C, 0.5 h, b) from -78 deg C to RT, 2 h, c) RT, 13 h 3: NH2OH*HCl, aq. NaOH / ethanol / 1.5 h / Heating View Scheme

1: 1.) LDA / 1.) THF, -78 deg C, 0.5 h, 2.) THF, a) -78 deg C, 0.5 h, b) from -78 deg C to RT, 2 h, c) RT, 13 h 2: NH2OH*HCl, aq. NaOH / ethanol / 1.5 h / Heating View Scheme

sodium hydroxide; hydroxylamine hydrochloride in ethanol; water 2.5 h; Heating;

hydrogenchloride in water 3 h; Heatingeffect of acid concentration in the hydrolysis; Product distribution;