Multi-step reaction with 9 steps
1: 67 percent / AlCl3 / 1,2-dichloro-ethane / 1.) from 5 deg C to RT, 30 min, 2.) reflux, 30 min
2: 76 percent / hydroxylamine hydrochloride, pyridine / 24 h / Heating
3: 98 percent / 1 h / Heating
4: 84 percent / sodium hydride / dimethylformamide / 0.67 h / 30 °C
5: 91 percent / pyridine hydrochloride / 2 h / 180 °C
6: 1.) sodium hydride (50percent suspension in oil) / 1.) DMF, RT, 1 h, 2.) 60 deg C, 2.5 h
7: 80 percent / 0.75 h / 205 °C
8: 75 percent / 15percent aq. NaOH / methanol / 3 h / Heating
9: 77 percent / K2CO3 / dimethylformamide / 1 h / 65 °C
With
pyridine; sodium hydroxide; aluminium trichloride; hydroxylamine hydrochloride; pyridine hydrochloride; sodium hydride; potassium carbonate;
In
methanol; 1,2-dichloro-ethane; N,N-dimethyl-formamide;
DOI:10.1021/jm00343a008