Chlorosuccinimide → HCID 70300013, compound

Participants

Reaction Steps

A solution of 7-amino-6-fluoro-3-methyl-1,2(2H)-benzisoxazole (3.5 g, 0.021 mole) in DMF (50 mL) was stirred, and a solution of N-chlorosuccinimide (2.8 g, 0.02 mole) in a minimum amount of DMF was added dropwise. Upon completion of addition, the reaction mixture was stirred for about 18 hours. After this time, the reaction mixture was poured into aqueous 10% lithium chloride and then thoroughly extracted with ether. The combined extracts were washed with aqueous 10% lithium chloride, dried with magnesium sulfate, and concentrated to a residue. The residue was subjected to silica gel column chromatography using 9:1 to 4:1 hexane and ethyl acetate to provide 2.6 grams of 7-amino-4-chloro-6-fluoro-3-methyl-1,2(2H)-benzisoxazole. The NMR spectrum was consistent with the proposed structure.

Provenance & Evidence