Multi-step reaction with 9 steps
1: 1.) aq. NaNO2, HCl, 2.) Cu, HCl / 1.) from 0 deg C to 4 deg C, 2.) 20 deg C, 4 h
2: aq. KOH / 1.5 h / 160 °C
3: 18 percent aq. HCl / 7 h / Heating
4: 60 percent / HCl / 8 h / Heating
5: 91 percent / LiAlH4 / 3 h / -30 °C
6: 93 percent / SOCl2 / CHCl3 / 2 h / Ambient temperature
7: 74 percent / dimethylformamide / 2 h / 90 °C
8: 80 percent / 80 percent aq. N2H4 / ethanol / 10 h / Heating
9: 1.) N,N'-carbonyldiimidazole / 1.) THF, reflux, 1 h, 2.) THF, RT, overnight
With
hydrogenchloride; potassium hydroxide; lithium aluminium tetrahydride; thionyl chloride; copper; hydrazine hydrate; 1,1'-carbonyldiimidazole; sodium nitrite;
In
ethanol; chloroform; N,N-dimethyl-formamide;
DOI:10.1021/jm9810349