Multi-step reaction with 7 steps
1: 33 percent / nitric acid, glacial acetic acid / 1.) RT, 40 min, 2.) from 45 to 50 deg C, 16 h
2: hydrogen / 5percent Pd/C / tetrahydrofuran / 2 h / 2068.6 Torr
3: tetrahydrofuran / 0.33 h / 60 °C
4: 71 percent / nitric acid, glacial acetic acid / 2 h / Ambient temperature
5: 96 percent / methanol; H2O / 1 h / 85 °C
6: 90 percent / NaNO2, H2SO4 / ethanol; H2O / 1.) from 0 to 5 deg C, 20 min, 2.) 85 deg C, 20 min, 3.) RT, 1 h
7: 1.) lithium bis(trimethylsilyl)amide / 1.) THF, 078 deg C, 2 h, 2.) THF, a) -78 deg C, 1 h, b) RT, 20 h
With
sulfuric acid; hydrogen; nitric acid; acetic acid; lithium hexamethyldisilazane; sodium nitrite;
palladium on activated charcoal;
In
tetrahydrofuran; methanol; ethanol; water;
DOI:10.1021/jm00046a020