Chloroacetyl chloride → 2-Chloro-N-(phenanthridin-6-ylmethyl)acetamide

Participants

Reaction Steps

Triethylamine (460 μL, 3.30 mmol), followed by a solution of chloroacetyl chloride (175 μL, 2.20 mmol) in CH2Cl2 (5 mL) were added dropwise over 5 minutes to a solution of the amine 8 (229 mg, 1.10 mmol) dissolved in CH2Cl2 (15 mL) at 0° C. The reaction mixture was then allowed to warm to ambient temperature and stirred for 2 hours. The solvent was removed under reduced pressure and the reaction crude purified via flash chromatography over silica eluting with a gradient of CH2Cl2 to 1% MeOH/99% CH2Cl2. Evaporation of the solvents under reduced pressure yielded the chloro 9 as an off-white solid (177 mg, 56.5% over three steps).

Provenance & Evidence