(4-Chlorophenyl)hydrazine → [2-(4-Chloro-phenyl)-4,5,6,7-tetrahydro-2H-indazol-3-yl]-cyclohexyl-acetic acid ethyl ester

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Reaction Steps

(4-Chloro-phenyl)-hydrazine (100 mg, 700 μmol; CAS Reg. No. 1073-69-4) was added to a solution of 2-cyclohexyl-3-oxo-3-(2-oxo-cyclohexyl)-propionic acid ethyl ester (206 mg, 700 μmol) in ethanol (4.7 ml). The reaction mixture was heated under reflux conditions for 6 h. The solvent was removed under reduced pressure. The residue was taken up in ice water/brine 1/1 and extracted two times with iPrOAc. The combined extracts were washed with ice water/brine 1/1 and dried over Na2SO4. After filtration the solvent was removed under reduced pressure to give a brown oil which was purified by preparative thick layer chromatography (silica gel, iPrOAc/heptane) to give the title compound (130 mg, 324 μmol; 46%) as orange solid. MS: m/e=401.2 [M+H+].

Provenance & Evidence