N,N-Dimethylaniline → Ethyl 5-(4-chloro-5-phenylphthalazin-1-yl)nicotinate

Participants

Reaction Conditions

Reaction Steps

To a solution of ethyl 5-(4-hydroxy-5-phenylphthalazin-1-yl)nicotinate (3.50 g, 9.42 mmol) in toluene (35 mL) was added POCl3 (26.4 mL, 283 mmol) followed by N,N-dimethylbenzenamine (1.5 mL, 9.42 mmol). The resulting mixture was heated in a sealed tube at 100° C. for 12 h. The reaction mixture was allowed to cool to room temperature and concentrated under reduced pressure. The residue was dissolved in EtOAc (200 mL) and washed with saturated NaHCO3 (2×50 mL) solution. The combined organic extracts were dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure to yield ethyl 5-(4-chloro-5-phenylphthalazin-1-yl)nicotinate (3.50 g) as a yellow solid with LC-MS purity of 47% which was taken for the next step without further purification. LCMS (Condition 12): retention time 0.97 min, [M+1]=390.0.

Provenance & Evidence