Multi-step reaction with 6 steps
1: 65 percent / 1N aq. NaOH / CH2Cl2 / 0.33 h / Ambient temperature
2: 1.) 1-chloroethyl chloroformate / 1.) CH2Cl2, RT, 1 h, 2.) MeOH, reflux, 1 h
3: 51 percent / Na2CO3 / dimethylformamide / 18 h / 100 °C
4: hydrazine hydrate / ethanol / 4 h / Heating
5: 1.) 1,1'-carbonyldiimidazole / 1.) DMF, RT, 4 h, 2.) DMF, RT, 18 h
6: 1.) NaH / 1.) DMF, RT, 4 h, 2.) DMF, RT, 18 h
With
sodium hydroxide; carbonochloridic acid 1-chloro-ethyl ester; sodium hydride; sodium carbonate; hydrazine hydrate; 1,1'-carbonyldiimidazole;
In
ethanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jm970857f