Chlorosuccinimide → N-hydroxy-6-methylpicolinimidoyl chloride

Participants

Reaction Steps

To a mixture of commercially available (E)-6-methylpicolinaldehyde oxime (2 g, 14.69 mmol) in DMF (25 mL) was added 1-chloropyrrolidine-2,5-dione (2.158 g, 16.16 mmol). The reaction mixture was stirred overnight at room temperature. LCMS shows reaction was complete. The reaction mixture was diluted with ethyl acetate and washed with saturated NaCl (×3). The organic layer was dried with MgSO4, filtered, and concentrated to yield 2.5 g of N-hydroxy-6-methylpicolinimidoyl chloride. MS (m+1)=171. HPLC Peak RT=0.79 minutes (Analytical Method B).

Provenance & Evidence