Pyrazine, 2-(chloromethyl)- → HCID 54520121, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 2-(chloromethyl)pyrazine (2.63 g, 20.5 mmol) (prepared according to Zhang, X.-A. et al., J. Am. Chem. Soc. 2008, 130, 15788-15789) in N,N-dimethylformamide (20 mL) was added potassium phthalimide (3.98 g, 21.5 mmol). The reaction mixture was heated for 16 h at 110° C., allowed to cool to ambient temperature and concentrated in vacuo. The residue was partitioned between dichloromethane (150 mL) and water (50 mL). The organic phase was washed with water (50 mL) and brine (2×20 mL), dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The residue was triturated in a mixture of ethyl acetate and hexanes (1:1) to afford 2-(pyrazin-2-ylmethyl)isoindoline-1,3-dione as a light brown solid in 73% yield (3.56 g): 1H NMR (300 MHz, CDCl3) δ8.63 (s, 1H), 8.45 (s, 2H), 7.89-7.83 (m, 2H), 7.76-7.70 (m, 2H), 5.03 (s, 2H); MS (ES+) m/z 240.0 (M+1).

Provenance & Evidence