Multi-step reaction with 11 steps
1: 1.) NaNO2, HBr, 2.) CuBr
2: 1.) tetrakis(triphenylphosphine)palladium(0), 2.) sodium carbonate / 1.) 1,2-dimethoxyethane, 20 min, 2.) 1,2-dimethoxyethane, water, reflux
3: 100 percent / hydrogen / Pd/C / ethanol / 1810.02 Torr
5: 99 percent / N-bromosuccinimide, benzoyl peroxide / CCl4 / 2 h / Heating
6: 80 percent / dimethylformamide / Ambient temperature
7: 92 percent / hydrazine hydrate / methanol / 1 h / Heating
8: 73 percent / sodium carbonate / CH2Cl2 / Ambient temperature
9: 1.) tetrakis(triphenylphosphine)palladium(0), 2.) sodium carbonate / 1.) 1,2-dimethoxyethane, 20 min, 2.) 1,2-dimethoxyethane, water, reflux, 20 min
10: thionyl chloride / diethyl ether / Heating
11: potassium tert-butoxide / tetrahydrofuran / 0 - 20 °C / other N-<2-(substituted phenyl)-6-(substituted aryl)benzyl>benzimidoyl chlorides, competing cyclisation on to the substituent in 2 position and in 6 position, other solvent: DMF
With
N-Bromosuccinimide; tetrakis(triphenylphosphine) palladium(0); thionyl chloride; Perbenzoic acid; potassium tert-butylate; hydrogen bromide; hydrogen; sodium carbonate; hydrazine hydrate; copper(I) bromide; sodium nitrite;
palladium on activated charcoal;
In
tetrahydrofuran; methanol; tetrachloromethane; diethyl ether; ethanol; dichloromethane; N,N-dimethyl-formamide;