Multi-step reaction with 7 steps
1: 43 percent / 1.) 70percent nitric acid, acetic anhydride / 1.) a) -15 deg C, 0.5 h, b) RT, 20 min
2: SOCl2 / tetrahydrofuran / 0.08 h / Heating
3: Hunig's base / tetrahydrofuran / -20 - 20 °C
4: 1.) H2, 2.) HCl / 10percent Pd/C / 1.) methanol, 40 deg C, 1 atm, 2.) isopropanol, -30 deg C
5: 64 percent / 1,8-bis(dimethylamino)naphthalene, dicyclohexylcarbodiimide / tetrahydrofuran; dimethylformamide / 3 h / Ambient temperature
6: 1.) HCl, 2.) NH3 / 1.) EtOH, RT, 1.5 h, 2.) EtOH, 1 h, RT
7: 70 percent / H2 / 10percent Pd/C / methanol / 40 °C
With
hydrogenchloride; thionyl chloride; ammonia; hydrogen; nitric acid; acetic anhydride; N,N,N',N'-tetramethyl-1,8-diaminonaphthalene; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide;
palladium on activated charcoal;
In
tetrahydrofuran; methanol; N,N-dimethyl-formamide;
DOI:10.1021/jo00220a019