4-Chlorobenzaldehyde → HCID 21847944, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 100 mg (0.345 mmol) of 1-(4-bromophenyl)-2-(4-pyridyl)-ethan-1,2-dione (from Step B), 266 mg (3.45 mmol) of ammonium acetate, and 61 mg (0.0.431 mmol) of 4-chlorobenzaldehyde in 2 mL of acetic acid was heated at 90° C. for 3 h. The green reaction mixture was treated with excess 2:1 NH4OH/sat. NH4Cl and extracted with ethyl acetate and chloroform 3 times. The organic layers were combined and washed with water, brine, and dried over sodium sulfate. After removal of solvents, the residue was flash chloromatographed over silica gel (gradient elution, 1-4% MeOH in DCM) to give 75 mg of the titled compound, homogeneous by TLC (9:1 DCM/MeOH); mass spectrum (CI) m/e 411, 413 (M+1)+.

Provenance & Evidence