Multi-step reaction with 11 steps
1: 1.) pyridine; 2.) H2O / 1.) 100 deg C, 30 min
2: SOCl2, DMF / 0.25 h / Heating
3: pyridine / CHCl3 / Heating
4: 45percent aq. KOH / methanol / 0.5 h
5: 92 percent / K2CO3, N-methylpyrrolidinone / 0.17 h / 140 °C
6: 81 percent / H2 / 5percent Pd/C / ethyl acetate; ethanol / 1 h / Ambient temperature
7: 78 percent / 1,8-bis(dimethylamino)naphthalene / 48 h / 125 °C
8: CF3COOH / CH2Cl2 / Ambient temperature
9: oxalyl chloride / CH2Cl2 / 0.17 h / Heating
10: 46 percent / ethanol; CH2Cl2 / Ambient temperature
11: 1M aq. tetramethylammonium hydroxide / methanol / Ambient temperature
With
pyridine; 1-methyl-pyrrolidin-2-one; potassium hydroxide; thionyl chloride; oxalyl dichloride; tetramethyl ammoniumhydroxide; water; hydrogen; N,N,N',N'-tetramethyl-1,8-diaminonaphthalene; potassium carbonate; N,N-dimethyl-formamide; trifluoroacetic acid;
palladium on activated charcoal;
In
methanol; ethanol; dichloromethane; chloroform; ethyl acetate;
DOI:10.1021/ja00202a042