Multi-step reaction with 8 steps
1: 94 percent / sodium cyanoborohydride, bromocresol green, acetic acid / ethanol / 48 h / Ambient temperature
2: 91 percent / sodium cyanoborohydride, bromocresol green, aq. acetic acid / acetonitrile / 1 h / Ambient temperature
3: 80 percent / hydrogen, HCl / palladium on carbon / ethanol / 3 h / 2482.3 Torr
4: aq. acetic acid / 1.) 0 deg C, 2.) room temperature, 17 h
5: 80 percent / pyridine / 1 h / Ambient temperature
6: 20 percent / dimethylformamide / 24 h / 90 - 100 °C
7: 42 percent / NaHCO3 / dimethylformamide / 2 h / Ambient temperature
8: 1.) Zn, Cu, acetylacetone, 2.) NaOH / 1.) DMF, 50 deg C to 55 deg C, 1.5 h, 2.) ethanol, 48 h
With
hydrogenchloride; sodium hydroxide; hydrogen; bromocresol green; copper; sodium cyanoborohydride; sodium hydrogencarbonate; acetic acid; acetylacetone; zinc;
palladium on activated charcoal;
In
pyridine; ethanol; acetic acid; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1021/jm00119a012